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

HRID 1453000Notes

Reaction equation

HRID 1453000 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

3

Reactant 2

HCID 7757Methyl acetoacetateHCID 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. 1H NMR (CDCl3): δ 1.35-1.86 (brm, 8H), 2.35 (m, 1H), 2.61-3.62 (m, 6H), 3.85 (s, 3H), 6.82 (d, J=8.2 Hz, 2H), 7.44 (d, J=8.2 Hz, 2H).

Sources & evidence

ORD record
ord-189dde5341ae4e60aa38a9d57b5c438e
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

Loading…