Water → (3-(Benzyloxy)cyclobutyl)methanol

HRID 1907314ノート

反応式

HRID 1907314 の反応式
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([C:13](O)=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 128151113-(Benzyloxy)cyclobutane-1-carboxylic acid

生成物 1

HCID 15221213(3-(Benzyloxy)cyclobutyl)methanol収率 93.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-benzyloxy-cyclobutanecarboxylic acid (1.67 g) in dry tetrahydrofuran (100 mL) was treated with borane-dimethylsulfide complex (1.3 mL) at 50° C. for 16 hours. Water (4 mL) and saturated sodium hydrogen carbonate (3 mL) were added and the mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in cyclohexane (0 to 1:1 by volume) to give the title compound (1.46 g). 1H NMR (400 MHz, CHCl3-d): δ 7.29 (d, 5H), 4.36 (d, 2H), 4.08 (t, 1H), 3.91-3.82 (m, 1H), 3.53 (t, 2H), 2.39-2.30 (m, 1H), 2.33-2.22 (m, 1H), 2.10-2.02 (m, 2H), 1.72-1.63 (m, 1H).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate in cyclohexane (0 to 1:1 by volume)

出典と根拠

ORDレコード
ord-18d5dd9a04a74c2fb14ab953e8312fc9
出典データセット
uspto-grants-2013_12
特許番号
US08598154B2

反応ノート

読み込み中…