Ammonium Chloride → HCID 67460415, compound

HRID 554485Notes

Reaction equation

HRID 554485 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][C:8]2[CH:9]=[C:10](Br)[CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.C([Li])CCC.[CH2:22]([O:29][CH:30]1[CH:35]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:34]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:33]([CH2:52][O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:32][C:31]1=[O:61])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>C1COCC1>[CH2:22]([O:29][C@@H:30]1[C@@H:35]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:34]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@@H:33]([CH2:52][O:53][CH2:54][C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH2:32][C:31]1([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][C:6]2[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:9]=1)[OH:61])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 14377830HCID 14377830, compoundHCID 22328603HCID 22328603, compoundHCID 178418339Butyllithium

Product 1

HCID 67460415HCID 67460415, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(4-methoxybenzyl)-1-bromobenzene (155 mg, 0.559 mmol) in THF (0.80 mL), an n-butyllithium 2.44 M hexane solution (0.23 mL, 0.559 mmol) was added dropwise at −78° C. and the mixture solution was stirred for 25 minutes. Then, a solution of 2,3,4-tribenzyloxy-5-(benzyloxy-methyl)cyclohexanone (200 mg, 0.373 mmol) in THF (0.70 mL) was added dropwise thereto and the reaction mixture was stirred for 75 minutes. To the reaction mixture was added a saturated ammonium chloride aqueous solution and the mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The solvent was concentrated and the obtained residue was purified by silica gel chromatography [developing solution=ethyl acetate:n-hexane (2:5)] to obtain the title compound (80 mg, 27%) as a mixture of 1R-isomer and 1S-isomer.

Workup

  1. stirringthe reaction mixture was stirred for 75 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated
  6. customthe obtained residue was purified by silica gel chromatography [developing solution=ethyl acetate:n-hexane (2:5)]

Sources & evidence

ORD record
ord-9755185475aa4f909f7e1848b2fa1b97
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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