Acetic Acid → (S)-1-Benzyloxy-3-(t-butyldiphenylsilyloxy)propan-2-ol

HRID 6256

반응식

HRID 6256 반응식
[CH2:1]([O:8][CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.N1C=CN=C1.[Si:23](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH2:1]([O:8][CH2:9][C@H:10]([OH:13])[CH2:11][O:12][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2724795(R)-3-(benzyloxy)propane-1,2-diol

생성물 1

HCID 10982698(S)-1-Benzyloxy-3-(t-butyldiphenylsilyloxy)propan-2-ol수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-3-benzyloxypropane-1,2-diol (prepared from (S)-4-benzylymethyl-2,2-dimethyl-1,3-dioxolane (commercially available from FLUKA) by acid hydrolysis using 80% aqueous acetic acid), (8.3 g, 47.2 mmol) in dry THF (70 ml) was added imidazole (6.42 g, 94.4 mmol). After 2 minutes, t-butyldiphenylsilyl chloride (12.28 ml, 47.2 mmol) was added. A white precipitate formed immediately. After 2 hours, the reaction mixture was filtered and the filtrate evaporated. The residue was partitioned between ethyl acetate and water, the organic layer separated, washed with saturated brine, dried (MgSO4), filtered and evaporated to give a colourless oil. Chromatography of the oil on silica gel (dichloromethane as eluant) afforded the title compound as a colourless oil (17.72 g, 90%).

후처리

  1. customby acid hydrolysis
  2. customA white precipitate formed immediately
  3. waitAfter 2 hours
  4. filtrationthe reaction mixture was filtered
  5. customthe filtrate evaporated
  6. customThe residue was partitioned between ethyl acetate and water
  7. customthe organic layer separated
  8. washwashed with saturated brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customto give a colourless oil

출처 및 근거

ORD 기록
ord-cf9e57ba9a5d488b84ad34a0e5f55896
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247085

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