Benzyl Bromide → Benzyl (s)-hexahydromandelate

HRID 1386667

反応式

HRID 1386667 の反応式
[C:1]([OH:11])(=[O:10])[C@H:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[OH:3].[OH-].[K+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)Cl>[C:1]([O:11][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:10])[C@H:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[OH:3]

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 819912(2s)-Cyclohexyl(hydroxy)acetic acid

生成物 1

HCID 54322505Benzyl (s)-hexahydromandelate収率 77.5%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6212Chloroform溶媒

反応条件

温度
70 °C

実験手順

A solution of 500 mg (3.2 mmol) of (S)-hexahydromandelic acid and 238 mg (0.6 mmol) of tetrabutylammonium iodide in 6.5 mL of CHCl3 was treated with 6.5 mL of 0.5 N KOH and 0.38 mL (3.2 mmol)of benzyl bromide then stirred at 70° C. for 1.5 h. The reaction was cooled to rt and the layers were separated. The aqueous phase was extracted with 2×50 mL CH2Cl2. The organic phases were combined, dried over Na2SO4 and concentrated. Flash chromatography using 17:3 v/v hexanes/EtOAc as the eluant afforded 616 mg (77%) of the title compound: RF: 0.37 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.11-1.38 (m, 11H), 2.65 (d, J=6.3 Hz, 1H), 4.06 (dd, J=6.3, 3.5 Hz, 1H), 5.22 (s, 2H), 7.30-7.39 (m, 5H).

後処理

  1. temperatureThe reaction was cooled to rt
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with 2×50 mL CH2Cl2
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-69b560becb814bccb0784c184fa67963
出典データセット
uspto-grants-2001_07
特許番号
US06265434B1

関連ノート

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