Ethyl Acetate → HCID 86677384, compound

HRID 39614Notes

Reaction equation

HRID 39614 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:17][C@@H:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@H:15]([CH2:26][CH2:27][C@@H](O[Si](C(C)(C)C)(C)C)CCCCC)[C@H:14]2[CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([OH:49])[CH:44]=2)(=O)=O)=CC=1.[H-].[Na+].C([O:55][CH2:56][CH3:57])(=O)C>C1COCC1>[Si:19]([O:18][C@H:16]1[C@H:15]([CH2:26][CH2:27][C@@H:56]([O:55][Si:19]([C:22]([CH3:24])([CH3:23])[CH3:25])([CH3:21])[CH3:20])[CH2:57][CH2:15][CH2:14][CH2:13][CH3:12])[C@H:14]2[CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[C:45]([OH:49])[C:44]=3[CH2:12][C@H:13]2[CH2:17]1)([C:22]([CH3:25])([CH3:23])[CH3:24])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86677385((1S,2S,3R,4R)-2-(3-hydroxybenzyl)-4-(tert-butyldimethylsilyoxy)-3-((S)-3-(tert-butyldimethylsilyoxy)octyl)cyclopentyl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86677384HCID 86677384, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A degassed solution of ((1S,2S,3R,4R)-2-(3-hydroxybenzyl)-4-(tert-butyldimethylsilyoxy)-3-((S)-3-(tert-butyldimethylsilyoxy)octyl)cyclopentyl)methyl 4-methylbenzenesulfonate (12.4 g, 0.017 mol) in anhydrous THF (250 ml) at 0° C. under nitrogen was treated with 60% sodium hydride (2.04 g, 0.051 mol). The resulting suspension was stirred for 4 hr at reflux. The reaction was then cooled to 10° C., diluted with ice cold brine (250 ml) and ethyl acetate (500 ml). The reaction mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield: 87%.

Workup

  1. temperatureat reflux
  2. customseparated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solid was filtered off
  6. customThe solvent was evaporated off under vacuum
  7. customThe crude product was purified by chromatography on silica gel using
  8. additiona mixture of hexane and ethyl acetate as a gradient eluent

Sources & evidence

ORD record
ord-ca05604a24cd46f498293eca1f9e682b
Source dataset
uspto-grants-2013_09
Patent number
US08524939B2

Reaction notes

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