Tetrahydrofuran → HCID 178471409, compound

HRID 726506Notes

Reaction equation

HRID 726506 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 178471409HCID 178471409, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5ce15233ac3344868d239d09bf7904c8
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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