Chloroacetone → 4-Methyl-3-(2-oxo-propylsulfanyl)-benzoic acid ethyl ester

HRID 1466840Notes

Reaction equation

HRID 1466840 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([S:12][Si](C(C)C)(C(C)C)C(C)C)[CH:6]=1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(N(CC)CC)C.Cl[CH2:50][C:51](=[O:53])[CH3:52]>C1COCC1>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([S:12][CH2:50][C:51](=[O:53])[CH3:52])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 667648104-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

Product 1

HCID 667651894-Methyl-3-(2-oxo-propylsulfanyl)-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester (crude from step 1) in THF (50 mL) at 0° C. was added TBAF (13.9 mmol, 13.9 mL of a 1.0 M solution in THF). After 25 minutes, triethylamine (34.7 mmol, 4.74 mL) was added, followed by chloroacetone (16.7 mmol, 1.33 mL). The reaction was stirred for an additional 5 minutes, then subjected to standard aqueous workup. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to afford the title compound.

Workup

  1. customThe crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5f8d441c6cb4414dbe1c94319b3b8cd0
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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