Water → 4-(3-Cyclohexyl-1-butoxyprop-2-yloxymethyl)-2-(2-methylphenyl)benzoic acid, methyl ester

HRID 1532874Notes

Reaction equation

[CH:1]1([CH2:7][C@H:8]([OH:15])[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].I[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH:21]=1.O>CN(C=O)C>[CH:1]1([CH2:7][CH:8]([O:15][CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])[CH:21]=2)[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-3-cyclohexyl-1-butoxy-2-propanol (example 1308D, 1.0 g) in DMF (15 mL) was added NaH (0.184 g of a 60% oil dispersion). After 15 min, the reaction was chilled to 0° C., and 4-iodomethyl-2-(2-methylphenyl)benzoic acid, methyl ester (example 1308E, 1.54 g) was added. After 45 min, the reaction was poured into water (150 mL), and extracted with EtOAc (2×75 mL). The organic extracts were washed with brine (20 mL), dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography eluting with 5% EtOAc/hexane to give a colorless oil (1.18 g, 62%).

Workup

waitAfter 45 min
extractionextracted with EtOAc (2×75 mL)
washThe organic extracts were washed with brine (20 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with 5% EtOAc/hexane

Sources & evidence

ORD record: ord-5c1aee4070b0448b8b194319776ebe4c
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06204293B1

Reaction notes

Loading…