Potassium Carbonate → 4-[2-(3-Hydroxymethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one

HRID 2171033Notes

Reaction equation

[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][C:16]2=[O:21].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1([CH2:34][OH:35])[CH2:33][O:32][CH2:31]1>C(#N)C>[OH:35][CH2:34][C:30]1([CH2:29][O:1][C:2]2[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=2[C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH2:15][C:16]3=[O:21])[CH2:33][O:32][CH2:31]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirring solution of 4-(2-Hydroxy-3,4-dimethoxy-phenyl)-indan-1-one (Compound 303) (500 mg, 1.76 mmol) in acetonitrile, were added potassium carbonate (728 mg, 5.28 mmol) and (3-Bromomethyl-oxetan-3-yl)-methanol (764 mg, 4.28 mmol) and the resultant reaction mixture was heated to 70° C. for 16 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-70% ethyl acetate in pet ether) afforded 4-(2-((3-(hydroxymethyl)oxetan-3-yl)methoxy)-3,4-dimethoxyphenyl)-indan-1-one (Compound 104) as a white solid.

Workup

customthe resultant reaction mixture
customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate (3×)
washThe combined ethyl acetate layer was washed with brine
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure
customPurification by column chromatography (silica gel, 0-70% ethyl acetate in pet ether)

Sources & evidence

ORD record: ord-79b87bb7a35944d2a7d92ff7fefc42a1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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