Sulfoxonium, trimethyl-, iodide (1:1) → 6-Fluoro-2-(oxiran-2-yl)chroman

HRID 1911956Notes

Reaction equation

[I-].C[S+](C)(C)=O.[CH3:7]C(C)([O-])C.[K+].[F:13][C:14]1[CH:15]=[CH:16][C:17]2[O:22][CH:21]([CH:23]=[O:24])[CH2:20][CH2:19][C:18]=2[CH:25]=1>CS(C)=O>[CH2:20]1[CH:21]([CH:23]2[O:24][CH2:7]2)[O:22][C:17]2[CH:16]=[CH:15][C:14]([F:13])=[CH:25][C:18]=2[CH2:19]1

Participants

Conditions

Temperature: 30 °C

Procedure

To 234 ml of dimethyl sulfoxide was added 32 g of trimethyl sulfoxonium iodide. To it, potassium tertiary butoxide (16 g) was added and stirred for 1 h at 20-40° C. The reaction mixture was cooled and to it was added a solution of the compound obtained in Example 2 in dimethyl sulfoxide (26 ml.) while maintaining the temperature between 20°-40° C. for 1.5 hr. The reaction mixture was quenched in cold water. The aqueous layer was extracted with ethyl acetate, washed with water, concentrated under reduced pressure followed by product distillation to give 19.6 g of 6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran (VII) in the form of a mixture of A and B as an oil.

Workup

temperatureThe reaction mixture was cooled and to it
temperaturewhile maintaining the temperature between 20°-40° C. for 1.5 hr
customThe reaction mixture was quenched in cold water
extractionThe aqueous layer was extracted with ethyl acetate
washwashed with water
concentrationconcentrated under reduced pressure
distillationfollowed by product distillation

Sources & evidence

ORD record: ord-9848df7bc52743119228972c7c83168d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604222B2

Reaction notes

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