Boron trifluoride → 1-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde

HRID 351435

反応式

HRID 351435 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)=[CH2:18])=[CH2:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][C:34](=[CH2:37])[CH:35]=[O:36].B(F)(F)F>C(Cl)Cl>[CH3:33][C:34]1([CH:35]=[O:36])[CH2:37][CH2:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:23][CH:24]=2)[CH2:18]1

参加物

5

反応物 3

HCID 6356Boron trifluorideHCID 6562MethacroleinHCID 184363312,3-Di(4-benzyloxy-phenyl)-1,3-butadiene

生成物 1

HCID 865958461-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2,3-di(4-benzyloxy-phenyl)-1,3-butadiene (1.2 g, 2.8 mmol) and 2-methyl-propenal (0.602 g, 8.4 mmol) in DCM (10.5 mL) was added BF3.OCH2CH3 (0.596 mL, 4.2 mmol) at −10° C. After 3 h at −10° C., the reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL). The reaction mixture was then extracted with ethyl acetate (2 10 mL), dried over MgSO4 and purified by SiO2 twice (15% ethyl acetate/hexane) to yield 1-methyl-3,4-di(4-benzyloxy-phenyl )-cyclohex-3-ene carbaldehyde.

後処理

  1. customat −10° C
  2. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL)
  3. extractionThe reaction mixture was then extracted with ethyl acetate (2 10 mL)
  4. dry with materialdried over MgSO4
  5. custompurified by SiO2 twice (15% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-cccc71e19d034744869a56f0a372cf5c
出典データセット
uspto-grants-2007_02
特許番号
US07183445B2

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