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

HRID 6256

Reaction equation

HRID 6256 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-cf9e57ba9a5d488b84ad34a0e5f55896
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Linked notes

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