Triethylamine → HCID 53891592, compound

HRID 977818Notes

Reaction equation

HRID 977818 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][CH3:11])[C:4]=1[NH:12][C:13](=[O:29])[CH2:14][CH:15]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:22][C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=O.[Br-].[CH2:31]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33].C(N(CC)CC)C.[BH4-].[Na+]>C(OCC)(=O)C.CO.O1CCCC1>[OH:33][CH:32]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH:31]=[CH:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][CH3:11])[C:4]=1[NH:12][C:13](=[O:29])[CH2:14][CH:15]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[O:22][C:23]2[C:28]1=[CH:27][CH:26]=[CH:25][CH:24]=2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 197064(2-Oxo-2-phenylethyl)(triphenyl)phosphanium bromideHCID 4311764Sodium borohydrideHCID 19966069HCID 19966069, compound

Product 1

HCID 53891592HCID 53891592, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

10 ml of a tetrahydrofuran suspension containing 152 mg (0.392 mmol) of N-(2-formyl-6-methoxymethylphenyl)-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 53), 199 mg (0.432 mmol) of phenacyltriphenylphosphoniumbromide and 48 mg (0.471 mmol) of triethylamine was heated for 6 hours under reflux. At the end of this time, the mixture was allowed to return to room temperature. 4 ml of methanol were added, and then 155 mg (4.10 mmol) of sodium borohydride were gradually added to the mixture, which was then stirred for 1 hour. The reaction solution was then diluted with ethyl acetate, and washed several times with water. The solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography through 20 g of silica gel. Elution with a 4:1 by volume mixture of methylene chloride and ethyl acetate afforded 126 mg (yield 66%) of the title compound as crystals, melting at 204.5-206.5° C. (after recrystallization from methanol).

Workup

  1. temperaturewas heated for 6 hours
  2. temperatureunder reflux
  3. customto return to room temperature
  4. washwashed several times with water
  5. customThe solvent was removed by distillation under reduced pressure
  6. washElution with a 4:1
  7. additionby volume mixture of methylene chloride and ethyl acetate
  8. customafforded

Sources & evidence

ORD record
ord-7d1114e5ffad492cb4cc1ca08777bd32
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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