Ethanethiol → HCID 15550461, compound

HRID 1596484Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:25]3[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=3)[S:8][C:7]=2[CH:33]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:18]=3)=[O:12])=[C:9]([C:25]3[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=3)[S:8][C:7]=2[CH:33]=1

Participants

Reactant 3

HCID 6343Ethanethiol

HCID 6451240Aluminum(III) Chloride

HCID 15338698HCID 15338698, compound

Product 1

HCID 15550461HCID 15550461, compound

Procedure

[6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl][4-carbomethoxymethoxyphenyl]methanone (250 mg, 0.54 mmol) was converted to the title compound by the procedure of Example 3 using 0.24 mL (3.25 mmol) of ethanethiol and 505 mg (3.79 mmol) of aluminum chloride except the total reaction time was 0.5 hours and the workup of the reaction went as follows: the mixture was poured into a mixture of brine/ethyl acetate and extracted with ethyl acetate. The residual solid remaining in the reaction vessel was dissolved in a minimal amount of methanol and added to the ethyl acetate extracts. The combined organic extracts were washed thoroughly with brine, dried (magnesium sulfate), filtered, and concentrated. Purification by radial chromatography (2 mm, silica gel, 40% methanol in ethyl acetate) gave 140 mg methyl ether cleaved product as a yellow solid.

Sources & evidence

ORD record: ord-5ef7fc803fb84fd18d5cfe45a760a1fb
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291484B1

Reaction notes

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