Dibromodifluoromethane → tert-butyl((3R,3aS,6aR)-6-(difluoromethylene)hexahydrofuro[3,2-b]furan-3-yloxy)dimethylsilane

HRID 2168161Notes

Reaction equation

HRID 2168161 reaction equation
[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C:16](=O)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:38](Br)([F:40])[F:39]>CN(C)C(=O)C>[C:4]([Si:1]([O:8][C@@H:9]1[CH2:10][O:11][C@@H:12]2[C:16](=[C:38]([F:40])[F:39])[CH2:15][O:14][C@H:13]12)([CH3:2])[CH3:3])([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 6382DibromodifluoromethaneHCID 11776TriphenylphosphineHCID 67049238(3aS,6R,6aS)-6-(tert-butyldimethylsilyloxy)tetrahydrofuro[3,2-b]furan-3(2H)-one

Product 1

HCID 67048710tert-butyl((3R,3aS,6aR)-6-(difluoromethylene)hexahydrofuro[3,2-b]furan-3-yloxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Alternatively, ketone (87) may be treated with triphenylphosphine and dibromodifluoromethane in N,N-dimethylacetamide to give tert-butyl((3R,3aS,6aR)-6-(difluoromethylene)hexahydrofuro[3,2-b]furan-3-yloxy)dimethylsilane (97) as detailed in Scheme 8.

Sources & evidence

ORD record
ord-544e58f1eaf046b5b3f4687665c137ba
Source dataset
uspto-grants-2015_06
Patent number
US09045492B2

Reaction notes

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