Sodium borohydride → 1-Hydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 963717ノート

反応式

HRID 963717 の反応式
[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH:23]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:24]2=[O:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.O1CCCC1>[OH:29][CH:24]1[C:25]2[C:20](=[C:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:22][CH:23]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 540112435-t-Butyldiphenylsilyloxy-2-ethoxycarbonyl-1-oxo-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 536494731-Hydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene収率 46.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-t-butyldiphenylsilyloxy-2-ethoxycarbonyl-1-oxo-1,2,3,4-tetrahydronaphthalene (17 g) in a mixture of ethanol (100 ml) and tetrahydrofuran (100 ml) was added NaBH4 (1.4 g) at 0° C. After the mixture was stirred for 6 hours at room temperature, the solvent was removed in vacuo. The residue was dissolved in a mixture of ethyl acetate and water and the organic solution was washed with 1N--HCl solution, sat. NaHCO3, and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 1-hydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (7.9 g).

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  3. washthe organic solution was washed with 1N
  4. customThe dried solvent was evaporated in vacuo
  5. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-ed7c78a4830141ad85a7e81a9b5c290a
出典データセット
uspto-grants-1998_06
特許番号
US05763489

反応ノート

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