Tetrahydrofuran → HCID 178471409, 화합물

HRID 726506노트

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HRID 726506 반응식
[Br-].[CH2:2]([O:4][C:5]([CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH3:3].[F:29][C:30]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=1[C@H:37]1[CH2:42][CH2:41][C@H:40]([CH:43]=O)[CH2:39][CH2:38]1.O1CCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O1CCCC1>CCOCC>[F:29][C:30]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=1[C@H:37]1[CH2:38][CH2:39][C@H:40]([CH:43]=[CH:9][CH2:8][CH2:7][C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:41][CH2:42]1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 2773643(3-(Ethoxycarbonyl)propyl)triphenylphosphonium BromideHCID 23700795NaHMDS tetrahydrofuranHCID 178520918HCID 178520918, 화합물

생성물 1

HCID 178471409HCID 178471409, 화합물수율 62%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

First, 25.7 g of 3-ethoxycarbonylpropyltriphenylphosphonium bromide, 10.1 g of trans-4-(2,3-difluorophenyl)cyclohexanecarbaldehyde, and 150 ml of dry tetrahydrofuran were placed in a 300 ml flask. Then, 56.3 ml of 1.0M sodium bis(trimethylsilyl)amide/tetrahydrofuran solution was added dropwise to the reaction mixture at -70° C. to -60° C. The reaction mixture was stirred while being allowed to warm to room temperature over 6 hours. Ether was added to the reaction mixture. The ether solution was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/1) to obtain 9.0 g of 2,3-difluoro-1-[trans-4-(4-ethoxycarbonyl-1-butenyl)cyclohexyl]benzene (Y: 62%). The compound thus obtained had a purity of 89.2% (mixture of E and Z isomers) by GC.

후처리

  1. washThe ether solution was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThereafter, the solvent was distilled away
  4. customThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/1)

출처 및 근거

ORD 기록
ord-5ce15233ac3344868d239d09bf7904c8
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05709911

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