Dimethyl Sulfoxide → Ethyl 2,2-bis(6-benzyloxyhexyl)acetate

HRID 1289383Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(C(OCC)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].CS(C)=O>O>[CH2:33]([O:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 180 °C

Procedure

First, 14.8 g of diethyl 2,2-bis(6-benzyloxyhexyl)malonate, 0.5 g of water, 2.3 g of lithium chloride, and 50 ml of dimethyl sulfoxide were placed in a 100 ml flask. Then, the mixture was stirred at 180° C. for 12 hours. The reaction mixture was poured into water, and an organic layer was extracted with methylene chloride. The methylene chloride layer 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: hexane/ethyl acetate=9/1) to obtain 9.4 g of ethyl 2,2-bis(6-benzyloxyhexyl)acetate (Y: 72.9%). The compound thus obtained had a purity of 97.9% by GC.

Workup

extractionan organic layer was extracted with methylene chloride
washThe methylene chloride layer was washed with water
dry with materialdried over anhydrous sodium sulfate
distillationThereafter, the solvent was distilled away
customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record: ord-7d19e26cf6574bff8faa4e75fcbbce05
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750213

Reaction notes

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