Methyl acetoacetate → 6-Cyclopentyl-6-(4-methoxy-phenylsulfanylmethyl)-dihydro-pyran-2,4-dione

HRID 858553Notes

Reaction equation

[CH:1]1([C:6](=[O:17])[CH2:7][S:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18](OC)(=[O:23])[CH2:19][C:20]([CH3:22])=[O:21]>>[CH:1]1([C:6]2([CH2:7][S:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[O:17][C:18](=[O:23])[CH2:19][C:20](=[O:21])[CH2:22]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 7757Methyl acetoacetate

HCID 587625451-Cyclopentyl-2-(4-methoxy-phenylsulfanyl)-ethanone

Product 1

HCID 104046646-Cyclopentyl-6-(4-methoxy-phenylsulfanylmethyl)-dihydro-pyran-2,4-dione

Procedure

1-Cyclopentyl-2-(4-methoxy-phenylsulfanyl)-ethanone (from Step 2 below) was subjected to the methyl acetoacetate dianion addition reaction described in the synthesis of Example A(82), to yield the title compound as a white solid.

Sources & evidence

ORD record: ord-0de4b1f24c3e462b8c8cc6e387d5970b
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Reaction notes

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