Methyl chloroacetate → HCID 67267336, compound

HRID 602751

Reaction equation

[C:1]1(S)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][O:19][C:20](=[O:23])[CH2:21]Cl.O[O:25][S:26]([O-:28])=O.[K+]>CC(=O)C>[CH3:18][O:19][C:20](=[O:23])[CH2:21][S:26]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1)(=[O:28])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of 3.1 g (0.019 mol) of naphthalene-1-thiol and 2.94 g (0.021 mol, 1.1 eq) of K2CO3 in 100 mL of propan-2-one cooled at 0° C., 3.15 g (0.029 mol, 1.5 eq) of chloro-acetic acid methyl ester were added in one portion. The ice bath was removed and the reaction mixture was stirred an additional 4 hours. The reaction was filtered, the solvent evaporated and the resulting residue was taken up in 100 mL of MeOH. 14.3 g (0.023 mol, 1.2 eq) of oxone (potassium peroxymonosulfate) were added and the reaction mixture was stirred over night at RT. The salts were filtered off, the solvent evaporated and the residue purified by column chromatography on silica gel with heptane/EtOAc (from 4:1 to 1:2) to afford 2.78 g (55%) of (naphthalene-1-sulfonyl)-acetic acid methyl ester as a light yellow oil, MS: 265 (MH+).

Workup

customThe ice bath was removed
filtrationThe reaction was filtered
customthe solvent evaporated
stirringthe reaction mixture was stirred over night at RT
filtrationThe salts were filtered off
customthe solvent evaporated
customthe residue purified by column chromatography on silica gel with heptane/EtOAc (from 4:1 to 1:2)

Sources & evidence

ORD record: ord-8b117963bb6648eeb711e6a3174dc962
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906546B2

Linked notes

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