Diisobutylaluminum hydride → 6-Cyclohexylidene-hexan-1-ol

HRID 9810ノート

反応式

HRID 9810 の反応式
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:9]1(=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:2])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 140222266-Cyclohexylidene-hexanoic acid methyl ester

生成物 1

HCID 140222306-Cyclohexylidene-hexan-1-ol収率 100.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To a stired solution of 6-cyclohexylidene-hexanoic acid methyl ester (1.28 g, 6.10 mmol) in toluene (60 mL) was added DIBAL-H (15.3 mL, 1 M solution in hexane, 15.3 mmol) dropwise at 0° C. under N2. After stirring at 0° C. for 30 min, the reaction was quenched by MeOH (5 mL). Saturated aqueous sodium potassium tartrate (40 mL) was added to the reaction mixture. After string for 1 h, the organic layer was separated and the aqueous phase was extracted with ether. The combined organic layers were washed with water and brine and dried. Evaporation of the solvent gave 6-cyclohexylidene-hexan-1-ol (1.12 g, 100%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.05 (1H, m), 3.62 (2H, t, J=6.6 Hz), 2.05 (6H, m), 1.42–1.64 (8H, m), 1.34 (2H, m); 13C NMR (75 MHz, CDCl3) δ 139.78, 121.25, 63.22, 37.43, 32.96, 30.22, 28.96, 28.11, 27.23, 25.58.

後処理

  1. customthe reaction was quenched by MeOH (5 mL)
  2. additionSaturated aqueous sodium potassium tartrate (40 mL) was added to the reaction mixture
  3. waitAfter string for 1 h
  4. customthe organic layer was separated
  5. extractionthe aqueous phase was extracted with ether
  6. washThe combined organic layers were washed with water and brine
  7. customdried
  8. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-e9218e557d5c420fa426c304c9a5e1f0
出典データセット
uspto-grants-2006_08
特許番号
US07091357B2

反応ノート

読み込み中…