3-Chloro-2-chloromethyl-1-propene → Ethyl 2-(4-bromophenyl)-4-(chloromethyl)pent-4-enoate

HRID 221970

반응식

HRID 221970 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:24][CH2:25][C:26]([CH2:28]Cl)=[CH2:27].C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:28][C:26]([CH2:25][Cl:24])=[CH2:27])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 158593-Chloro-2-chloromethyl-1-propeneHCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 7020609Ethyl 2-(4-bromophenyl)acetate

생성물 1

HCID 59161543Ethyl 2-(4-bromophenyl)-4-(chloromethyl)pent-4-enoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of ethyl (4-bromophenyl)acetate (143 g, 588 mmol) in THF (800 mL) was added LHMDS (1.13 eq in THF) at −78° C. After 30 minutes, the reaction mixture was added to a solution of 3-chloro-2-chloromethyl-1-propene (147 g, 1180 mmol) in THF (500 mL) at −78° C. via cannula. The reaction was allowed to slowly warm from −78° C. to rt over 15 hours. The reaction mixture was poured into sodium bicarbonate, extracted with EtOAc, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by column chromatography eluting with 1-20% EtOAc/Hexane. The appropriate fractions were combined and the solvent removed in vacuo to give ethyl 2-(4-bromophenyl)-4-(chloromethyl)pent-4-enoate (1-1) as a clear oil. MS (M+H)+: 332.

후처리

  1. temperatureto slowly warm from −78° C. to rt over 15 hours
  2. extractionextracted with EtOAc
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by column chromatography
  7. washeluting with 1-20% EtOAc/Hexane
  8. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-2fe2a5c6810a4b97933ac6b5f2bffc25
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207169B2

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