Oxalyl chloride → HCID 68534728, compound

HRID 1992909Notes

Reaction equation

HRID 1992909 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:14][CH2:15][CH3:16])[CH2:10][C:11]([OH:13])=O)=[CH:4][C:3]=1[O:17][CH3:18].C(Cl)(=O)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]2[C:5]([CH2:8][CH:9]([CH2:14][CH2:15][CH3:16])[CH2:10][C:11]2=[O:13])=[CH:4][C:3]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 68536302HCID 68536302, compound

Product 1

HCID 68534728HCID 68534728, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-{[4-Fluoro-3-(methyloxy)phenyl]methyl}hexanoic acid (132) (1.92 g, 7.55 mmol) was treated with oxalyl chloride followed by AlCl3 in CH2Cl2 to give 1.70 g (95%) of the title compound (133) as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.90-0.95 (m, 3H), 1.35-1.45 (m, 4H), 2.10-2.30 (m, 2H), 2.60-2.75 (m, 2H), 2.90-3.00 (m, 1H), 3.93 (s, 3H), 6.74 (d, J=7.7 Hz, 1H), 7.70 (d, J=11.5 Hz, 1H). LCMS (ESI): m/z 236 (M+H)+.

Sources & evidence

ORD record
ord-8f7db6ad207f445a9303df6f238c4f65
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…