Dimethyl Sulfoxide → HCID 18651183, compound

HRID 1590405Notes

Reaction equation

HRID 1590405 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:11][C@H:10]2/[CH:12]=[C:13](\[F:16])/[CH2:14][OH:15])[CH:5]=[CH:6][C:7]=1[Cl:8].C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:11][C@H:10]2/[CH:12]=[C:13](\[F:16])/[CH:14]=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18651184HCID 18651184, compound

Product 1

HCID 18651183HCID 18651183, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above alcohol (3.3 g) was oxidised using the conditions of Swern oxalyl chloride, 1.2 ml; dimethyl sulphoxide, 2.0 ml; triethylamine, 8.8 ml] in dichloromethane to give (±)-(2Z)-3-[trans-2-(3,4-dichlorophenyl)cyclopropyl]-2-fluoroprop-2-enal (3.25 g). NMR 1H: 9.20(1H,d), 7.39(1H,d), 7.22(1H,d), 6.95(1H,dd), 5.60(1H,dd), 2.20(2H,m), 1.50(2H,m).

Sources & evidence

ORD record
ord-07bd2e5ef8b4445aa93509b4ced442fb
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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