Dimethyl Sulfoxide → HCID 19812057, compound

HRID 373205Notes

Reaction equation

HRID 373205 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:16])[CH3:15].CS(C)=O.C(Cl)(=O)C(Cl)=O>C(N(CC)CC)C>[F:1][C:2]([F:24])([F:25])[C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:19]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 19812072HCID 19812072, compound

Product 1

HCID 19812057HCID 19812057, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The above alcohol (16.17 mmol) was oxidised using methods described in EP-A-164 187 (Swern oxidation, DMSO, oxalyl chloride, triethylamine) to give 8-(3',5'-bistrifluoromethylbenzyloxy)-octan-2-one. The ketone was reacted with triethyl-4-phosphonocrotonate/lithium diisopropylamide to give ethyl 11-(3',5'-bistrifluoromethyl)benzyloxy- 5-methylundeca-2,4-dienoate. The ester was converted into the amide as in Example 5.

Sources & evidence

ORD record
ord-b22368d5dce94bbf9bb6926e24aef25e
Source dataset
uspto-grants-1992_11
Patent number
US05162367

Reaction notes

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