Benzene → 8-tert-Butyl-4,4-dimethyl-6-(1-oxopentyl)-thiochromane

HRID 1872858Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[S:13][CH2:12][CH2:11][C:10]2([CH3:16])[CH3:15])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Sn](Cl)(Cl)(Cl)Cl.C([O:26][CH2:27][CH3:28])(=O)C.[CH:29]1[CH:34]=CC=C[CH:30]=1>CCOCC>[C:1]([C:5]1[CH:6]=[C:7]([C:27](=[O:26])[CH2:28][CH2:30][CH2:29][CH3:34])[CH:8]=[C:9]2[C:14]=1[S:13][CH2:12][CH2:11][C:10]2([CH3:16])[CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To 500 mg (2.1 mmol) of 8-tert-butyl-4,4-dimethylthiochromane and 0.29 mL (2.34 mmol) of pentlanoyl chloride in 10 mL benzene at 0° C. is added 0.27 mL (2.34 mmol) of tin tetrachloride. The reaction is allowed to stir 1 hour at 0° C. and is then diluted with ether and washed with water and 10% sodium chloride. The product is purified by flash silica gel chromatography, eluting with 7:3 hexane:ethyl acetate to give 250 mg (37% yield) of the title compound.

Workup

washwashed with water and 10% sodium chloride
customThe product is purified by flash silica gel chromatography
washeluting with 7:3 hexane

Sources & evidence

ORD record: ord-03e2d76974674705834957145ca0c799
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110960

Reaction notes

Loading…