Dimethyl Sulfoxide → HCID 19801138, compound

HRID 1646544Notes

Reaction equation

HRID 1646544 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>ClCCl>[F:1][C:2]([F:23])([F:24])[C:3]1[CH:4]=[C:5]([CH:16]=[C:17]([C:19]([F:20])([F:22])[F:21])[CH:18]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19801151HCID 19801151, compound

Product 1

HCID 19801138HCID 19801138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above alcohol (1 g) was oxidised under Swern conditions (dimethyl sulphoxide (450 mg), oxalyl chloride (248 μl), triethylamine (1.58 ml)) in dichloromethane (25 ml) to give 7-(3,5-bistrifluoromethylbenzyloxy)heptan-1al. This was used directly in the next stage.

Sources & evidence

ORD record
ord-ffa27d90b557401e812ccff9e1d325c0
Source dataset
uspto-grants-1993_01
Patent number
US05180737

Reaction notes

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