Chloroform → {3-[(Tert-butyldimethylsilyl)oxy]-4-methoxyphenyl}methanol

HRID 1028923ノート

反応式

HRID 1028923 の反応式
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].C(Cl)(Cl)Cl>CO>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6212ChloroformHCID 3595583-((tert-Butyldimethylsilyl)oxy)-4-methoxybenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 11572549{3-[(Tert-butyldimethylsilyl)oxy]-4-methoxyphenyl}methanol収率 73.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a cooled solution of 3-[(tert-Butyldimethylsilyl)oxy]-4-methoxybenzaldehyde 13 (17.5 g, 65.7 mmol) in methanol (100 mL) under nitrogen, sodium borohydride (2.98 g, 78.8 mmol) was added and stirred at room temperature for 30 min. After the reaction was complete as indicated by TLC (chloroform on silica gel plate), ice was added to the reaction mixture and extracted with ethyl acetate. The organic layer was separated, washed with water and dried. Removal of solvent in vacuo yielded on yellow oil 14 (73.5%). 1H NMR: δ 0.18 (s, 6H, 2×CH3), 1.00 (s, 9H, 3×CH3), 1.90 (br s, 1H, OH), 3.82 (s, 3H, OCH3), 4.56 (s, 2H, CH2OH), 6.94 (br s, 3H, Ar—H). Anal. Calcd for C14H24O3Si: C, 62.64, H, 9.01. Found: C, 62.59, H, 9.03.

後処理

  1. additionwas added to the reaction mixture
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customRemoval of solvent in vacuo

出典と根拠

ORDレコード
ord-733c8dd9dd1245078779f65fc303d88b
出典データセット
uspto-grants-2014_05
特許番号
US08735620B2

反応ノート

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