Triethylamine → z-1-{4-[2-(2-Benzyloxyethoxy)ethoxy]phenyl}-4-chloro-1,2-diphenyl-but-1-ene

HRID 2181424Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(O)[CH:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23][CH2:24]O)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(Cl)([Cl:48])=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18](/[C:21](/[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:22](\[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)/[CH2:23][CH2:24][Cl:48])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

1-{4-[2-(2-Benzyloxy-ethoxy)ethoxy]phenyl}-1,2-diphenyl-butane-1,4-diol (10.0 g, 19.5 mmol) is dissolved in toluene (50 ml). Triethylamine (2.17 g, 21.4 mmol) is added to the solution and the mixture is cooled to −10° C. Thionyl chloride (6.9 g, 58.5 mmol) is added to the mixture at −10-±0° C. The mixture is stirred for 1 hour at 0-5° C., warmed up to 70° C. and stirred at this temperature for 4 hours. Solvent is evaporated, the residue is dissolved to toluene, washed three times with 1M HCl solution and twice with water. The Z-isomer of the product is crystallized from isopropanol-ethyl acetate. Yield 3.0 g. The filtrate is purified by flash chromatography to give E-isomer.

Workup

temperaturewarmed up to 70° C.
stirringstirred at this temperature for 4 hours
customSolvent is evaporated
dissolutionthe residue is dissolved to toluene
washwashed three times with 1M HCl solution
customThe Z-isomer of the product is crystallized from isopropanol-ethyl acetate
customThe filtrate is purified by flash chromatography
customto give E-isomer

Sources & evidence

ORD record: ord-06e7cf47e3904e51a3913ffcc144d410
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06891070B2

Reaction notes

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