2-Butenoic acid, 4,4-dimethoxy-, methyl ester, (Z)- → Methyl 4-p-tolylsulfonyl-4-methyl-3-dimethoxymethylpentanoate

HRID 236056

Reaction equation

C([Li])CCC.[CH:6]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:8])[CH3:7].[CH3:19][O:20][CH:21]([O:28][CH3:29])[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[O:25].P(O)(O)([O-])=O.[Na+]>C1CCCCC1.O1CCCC1>[C:15]1([CH3:18])[CH:16]=[CH:17][C:12]([S:9]([C:6]([CH3:7])([CH3:8])[CH:22]([CH:21]([O:28][CH3:29])[O:20][CH3:19])[CH2:23][C:24]([O:26][CH3:27])=[O:25])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: -70 °C

Procedure

3.4 ml of a 1.95M butyllithium in cyclohexane solution were slowly added at -70° C. to a solution of 1.24 g of p-tolyl isopropyl sulfone in 13 ml of tetrahydrofuran and the mixture was stirred at -70° C. for 15 minutes. Then, a solution of 1 g of methyl 4,4-dimethoxy-2-butenoate in 20 ml of tetrahydrofuran was slowly added to the mixture which was stirred at -70° C. for one hour and poured into a aqueous monosodium phosphate solution. The mixture was extracted with methylene chloride and the organic phase was dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 1--1 ether-petroleum ether (b.p.=40°-70° C.) mixture to obtain 1.1 g of methyl 4-p-toluenesulfonyl-4-methyl-3-dimethoxymethyl-pentanoate melting at 110° C.

Workup

stirringwas stirred at -70° C. for one hour
extractionThe mixture was extracted with methylene chloride
customthe organic phase was dried
customevaporated to dryness under reduced pressure
customThe residue was chromatographed over silica gel
washwas eluted with a 1--1 ether-petroleum ether (b.p.=40°-70° C.) mixture

Sources & evidence

ORD record: ord-47f976d2918344008a7a71679f3e0649
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642372

Linked notes

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