Ammonium Chloride → HCID 54309971, compound

HRID 977844Notes

Reaction equation

HRID 977844 reaction equation
[Br-].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][C:7]=1[NH:32][C:33](=[O:49])[CH2:34][CH:35]1[C:48]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[O:42][C:41]2[C:36]1=[CH:37][CH:38]=[CH:39][CH:40]=2)([CH3:5])([CH3:4])[CH3:3].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[CH2:60]([O:67][CH2:68][C:69](=O)[CH2:70][CH2:71][CH2:72][CH:73]1[CH2:78][CH2:77][CH2:76][CH2:75][CH2:74]1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[C:69]([CH2:68][O:67][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH2:70][CH2:71][CH2:72][CH:73]2[CH2:78][CH2:77][CH2:76][CH2:75][CH2:74]2)=[CH:8][C:7]=1[NH:32][C:33](=[O:49])[CH2:34][CH:35]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=2[O:42][C:43]2[C:48]1=[CH:47][CH:46]=[CH:45][CH:44]=2)([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 19966066HCID 19966066, compoundHCID 19966088HCID 19966088, compound

Product 1

HCID 54309971HCID 54309971, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1.36 g (1.87 mmol) of [4-t-butyl-3-[2-(9H-xanthen-9-yl)acetamido]phenyl]methyltriphenylphosphonium bromide (prepared as described in Preparation 34) in 15 ml of tetrahydrofuran was ice-cooled, and 2.10 ml (2.10 mmol) of a 1.0M tetrahydrofuran solution of sodium hexamethyldisilazide were added dropwise thereto over the course of 3 minutes. After 35 minutes, a solution of 511 mg (1.86 mmol) of 1-benzyloxy-5-cyclohexyl-2-pentanone (prepared as described in Preparation 35) in 5 ml of tetrahydrofuran was added to the mixture. The resulting mixture was stirred for 10 minutes whilst ice-cooling, at room temperature for 35 minutes and finally at 50° C. for 4.5 hours. At the end of this time, the temperature of the reaction mixture was lowered to room temperature, and then a saturated aqueous solution of ammonium chloride was added, in order to stop the reaction. The reaction mixture was then diluted with ethyl acetate and the diluted mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 100 g of silica gel, using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent, to give 781 mg (yield 65%) of the title compound as a foam-like material.

Workup

  1. temperaturecooled
  2. customover the course of 3 minutes
  3. customwas lowered to room temperature
  4. customthe reaction
  5. washthe diluted mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe resulting residue was purified by column chromatography through 100 g of silica gel
  9. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-dd931b2292624d2e9ad30da129d67ac4
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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