Iodoethane → 2-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid ethyl ester

HRID 1517539ノート

反応式

HRID 1517539 の反応式
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([O:28][CH3:29])=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:37][CH3:38]>CN(C=O)C>[CH2:37]([O:18][C:17](=[O:19])[C:16]1[CH:20]=[C:21]([O:28][CH3:29])[C:22]([C:24]([CH3:26])([CH3:25])[CH3:27])=[CH:23][C:15]=1[C:14]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:38]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 673744112-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid

生成物 1

HCID 673750432-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid ethyl ester収率 99.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

step 1—To a solution of 76 (100 mg, 0.26 mmol) in DMF (3 mL) were added Cs2CO3 (101 mg, 0.31 mmol) and iodoethane (25 μL, 0.31 mmol). The reaction mixture was stirred at RT overnight then quenched with H2O and thrice extracted with EtOAc. The combined organics were washed with H2O (3×), dried (MgSO4), filtered and concentrated under reduced pressure to afford 109 mg (99%) of 2-(2-benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid ethyl ester (78) as a pale yellow foam.

後処理

  1. customthen quenched with H2O and thrice
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with H2O (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-39949e6499324b66af7f169f55b6ece4
出典データセット
uspto-grants-2012_07
特許番号
US08232271B2

反応ノート

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