Ammonium Chloride → HCID 13964339, compound

HRID 1682264Notes

Reaction equation

HRID 1682264 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([CH2:16][C:17]#[C:18][Si](C)(C)C)[C@H:10]1/[CH:23]=[CH:24]/[C@@H:25]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[O-].[Na+].[Cl-].[NH4+]>CO>[Si:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([CH2:16][C:17]#[CH:18])[C@H:10]1/[CH:23]=[CH:24]/[C@@H:25]([O:31][Si:32]([C:35]([CH3:36])([CH3:38])[CH3:37])([CH3:34])[CH3:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 15659427HCID 15659427, compound

Product 1

HCID 13964339HCID 13964339, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

64.0 g (110 mmoles) of (1R,2R,3R,4S)-1-t-butyldimethylsilyloxy-2-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-4-hydroxymethyl-3-(3-trimethylsilyl-2-propynyl)cyclopentane (31) was taken into a 1-liter eggplant-shaped flask, and dissolved by adding 500 ml of methanol. Then, 106.3 g of a 28% methanol solution of sodium methylate was added, and the mixture was stirred at room temperature for 30 minutes. Saturated aqueous ammonium chloride solution (300 ml) was added, and the mixture was extracted twice with ethyl acetate. The organic layer was successively washed with saturated aqueous potassium hydrogensulfate solution, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 53.9 g (yield 96%) of (1R,2R,3R,4S)-1-t-butyldimethylsilyloxy-2-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-4-hydroxymethyl-3-(2-propynyl)cyclopentane (32) from eluates obtained with 10% ethyl acetate/n-hexane.

Workup

  1. dissolutiondissolved
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe organic layer was successively washed with saturated aqueous potassium hydrogensulfate solution, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40ede16999d145f18575a77dc9c885d6
Source dataset
uspto-grants-1992_12
Patent number
US05175338

Reaction notes

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