Water → HCID 178468872, 화합물

HRID 1035707노트

반응식

HRID 1035707 반응식
[O:1]1[C:3]2([CH2:8][CH2:7][CH:6]([C:9]3[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=3)[CH2:5][CH2:4]2)[CH2:2]1.B(F)(F)F.CCOCC.O>ClCCl>[CH:2]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=2)[CH2:5][CH2:4]1)=[O:1]

참가 물질

5

반응물 3

HCID 962WaterHCID 8000Boron trifluoride etherate2회HCID 86662113Ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate

생성물 1

HCID 178468872HCID 178468872, 화합물수율 45.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1.4 g of ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate (5.38 mmol, 1.4 eq.) are placed in 40 mL of dichloromethane at 4° C. 0.229 g of boron trifluoride etherate (1.61 mmol, 0.3 eq.) is added with stirring. After 2 hours, 0.153 g of boron trifluoride etherate (1.07 mmol, 0.2 eq.) is added. After 1 hour, water is added and the reaction medium is extracted three times with dichloromethane. The organic phases are combined and washed successively with saturated aqueous sodium hydrogen carbonate solution and water. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel with an 88/10/2 mixture of heptane/ethyl acetate/methanol. 0.64 g of ethyl trans-4-(4-formylcyclohexyl)benzoate is obtained.

후처리

  1. waitAfter 1 hour
  2. extractionthe reaction medium is extracted three times with dichloromethane
  3. washwashed successively with saturated aqueous sodium hydrogen carbonate solution and water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel with an 88/10/2 mixture of heptane/ethyl acetate/methanol

출처 및 근거

ORD 기록
ord-1dec5afe689e4f9a80102dbc984cf48d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546391B2

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