Sodium Chloride → 8-Methylsulfonyl-12-hydroxy-13-(4-fluorophenoxy)tridecanoic acid

HRID 65653Notes

Reaction equation

[CH3:1][S:2]([C:5](C(OC)=O)([CH2:16][CH2:17][CH2:18][CH:19]([O:29]CC1C=CC=CC=1)[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])(=[O:4])=[O:3].[Cl-].[Na+].CN(C)C=O>O>[CH3:1][S:2]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([OH:29])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:4])=[O:3]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of methyl 8-methylsulfonyl-8-methoxycarbonyl-12-benzyloxy-13-(4-fluorophenoxy)tridecanoate (2.60 g., 4.5 mmoles), sodium chloride (0.5 g., 8.5 mmoles), dimethylformamide (8 ml.) and water (0.2 ml.) is heated with an oil bath at 160° C. overnight (ca. 15 hours). The reaction mixture is allowed to cool to room temperature, quenched with cold water, and then extracted with chloroform three times. The combined extracts are washed with brine and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation in vacuo leaving the desired product as a viscous oil residue (2.30 g., 4.4 mmoles, 98%). ir (neat) 3.40, 5.72, 6.20, 6.62, 6.87, 7.71, 8.00, 8.28, 8.90, 12.04, 13.17, 14.37μ; pmr CCl4) δ 1.0-2.9 (22H, m, containing a methyl singlet at 2.60 δ), 3.54 (3H, s); 3.5-4.1 (3H, m), 4.47 (1H, d, J=12Hz), 4.70 (1H, d, J= 12Hz), 6.6-7.1 (4H, m), 7.20 (5H, s).

Workup

temperatureto cool to room temperature
customquenched with cold water
extractionextracted with chloroform three times
washThe combined extracts are washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent is removed by evaporation in vacuo

Sources & evidence

ORD record: ord-7bb42c3962474a54b1c559d3589035a8
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04128564

Reaction notes

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