Sodium borohydride → HCID 18367371, compound

HRID 1741398Notes

Reaction equation

HRID 1741398 reaction equation
[BH4-].[Na+].[Si:3]([O:20][C:21]1[CH:22]=[C:23]([CH:51]=[CH:52][CH:53]=1)[CH2:24][CH:25]([C:32]([C:34]1[O:35][C:36]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:38]=1)=O)[CH2:26][C:27]([O:29]CC)=[O:28])([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C1C=CC=CC=1>CO.COCCOC>[Si:3]([O:20][C:21]1[CH:22]=[C:23]([CH:51]=[CH:52][CH:53]=1)[CH2:24][CH:25]1[CH2:26][C:27](=[O:28])[O:29][CH:32]1[C:34]1[O:35][C:36]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:38]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18367225HCID 18367225, compound

Product 1

HCID 18367371HCID 18367371, compoundYield 181.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

NaBH4 (119 mg) was added to a stirred solution of ethyl 3-[3-(tert-butyldiphenylsilyloxy)benzyl]-4- (4,5-diphenyl-2-oxazolyl)-4-oxobutyrate (430 mg) in methanol (2.0 ml) and 1,2-dimethoxyethane (0.5 ml) at room temperature and the resulting mixture was stirred at the same temperature for 3 hours. The reaction mixture was partitioned between ethyl acetate -1N hydrochloric acid. The organic layer was washed with 1N hydrochloric acid, aqueous sodium bicarbonate, and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 3-[3-(tert-butyldiphenylsilyloxy)benzyl]-2- (4,5-diphenyl-2-oxazolyl)-5-oxotetrahydrofuran (366 mg) as an amorphous powder. NMR (CDCl3, δ): 1.08 and 1.09 (9H, each s), 1.40-1.62 (1H, m), 2.31-2.97 (2H, m), 3.48-3.88 (2H, m), 4.58 and 4.80 (1H, each m), 6.54-7.05 (2H, m), 7.32-7.73 (22H, m)

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate -1N hydrochloric acid
  2. washThe organic layer was washed with 1N hydrochloric acid, aqueous sodium bicarbonate, and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-3f8936a4e110475f8e2d559ff8dff496
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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