Dimethylformamide → 5-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one

HRID 460340Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2.[Cl-].[Li+].CN(C=O)C>O>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 5,6 dimethoxyindan-1-one (25.0 g, 0.13 mole), lithium chloride (20.0 g, 0.47 mole) and DMF (200.0 mL) was stirred at 160° C. for 60 hrs. Water (400.0 mL) was added and the mixture washed with ethyl acetate. The aqueous layer was acidified with 2N HCl and extracted with ethyl acetate (2×300.0 mL). The organic layer was washed with brine and the solvent removed in vacuo. The crude material was purified on a silica gel column using DCM/MeOH(97/3) as the eluent. The solvent was removed in vacuo to yield 5-hydroxy-6-methoxy-indan-1-one (Intermediate H) as a light yellow solid. MS m/z 179 (M+H)+: 179 m/z. The title compound (Intermediate H) is a known compound and may also be prepared by demethylation of 5,6 dimethyoxyindan-1-one using KCN/DMSO at 100° C. (J. M. Saa et al., J. Org. Chem. 1992, 57, 589).

Workup

washthe mixture washed with ethyl acetate
extractionextracted with ethyl acetate (2×300.0 mL)
washThe organic layer was washed with brine
customthe solvent removed in vacuo
customThe crude material was purified on a silica gel column
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-a2931869f6ed448b941e89ebec6adf04
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196110B2

Reaction notes

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