Oxalyl chloride → 2-Acetoxy-4-methyl-cyclohexanecarboxylic acid chloride

HRID 749374ノート

反応式

HRID 749374 の反応式
[C:1]([O:4][C@H:5]1[CH2:10][C@H:9]([CH3:11])[CH2:8][CH2:7][C@H:6]1[C:12]([OH:14])=O)(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C)C=O>[C:1]([O:4][CH:5]1[CH2:10][CH:9]([CH3:11])[CH2:8][CH2:7][CH:6]1[C:12]([Cl:18])=[O:14])(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 57457642(1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid

生成物 1

HCID 597523912-Acetoxy-4-methyl-cyclohexanecarboxylic acid chloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (1R, 2S, 4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid (109 mg, 0.54 mmol) in dichloromethane (2.7 ml) was added oxalyl chloride (545 ul, 1.09 mmol) followed by 1 drop of dimethylformamide. The reaction mixture was stirred for 4 h at room temperature. The solvents were then removed to obtain 119 mg (99%) of (1R*, 2S*, 4R*)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid chloride. NMR 1H (CDCl3, 400 MHz): 5.45 ppm (s, 1H); 2.46-2.42 ppm (m, 1H); 2.02 ppm (s, 3H); 2.02-1.96 ppm (m, 1H); 1.91-1.76 ppm (m, 3H); 1.70-1.61 ppm (m, 1H); 1.16-1.08 ppm (m, 1H); 0.99-0.88 ppm (m, 1H); 0.87 ppm (d, 3H).

後処理

  1. customThe solvents were then removed

出典と根拠

ORDレコード
ord-7905997cee90436d86ca7c8568e99f1e
出典データセット
uspto-grants-2008_07
特許番号
US07402608B2

反応ノート

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