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

HRID 6256

反応式

HRID 6256 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-cf9e57ba9a5d488b84ad34a0e5f55896
出典データセット
uspto-grants-1993_09
特許番号
US05247085

関連ノート

読み込み中…