alpha-Chlorohydrin, (+)- → 3-[4-((S)-2,3-dihydroxy-propoxy)-3,5-dimethyl-phenyl]-1-(5-ethyl-4-o-tolyl-thiophen-2-yl)-propan-1-one

HRID 552289Notes

Reaction equation

[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:20])[CH2:9][CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([CH3:19])[CH:12]=2)=[CH:5][C:4]=1C1C=CC(C)=CC=1)[CH3:2].Cl[CH2:29][C@@H:30]([OH:33])[CH2:31][OH:32]>C(O)C.[OH-].[Na+]>[OH:33][C@@H:30]([CH2:31][OH:32])[CH2:29][O:18][C:14]1[C:15]([CH3:17])=[CH:16][C:11]([CH2:10][CH2:9][C:8]([C:6]2[S:7][C:3]([CH2:1][CH3:2])=[C:4]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH3:10])[CH:5]=2)=[O:20])=[CH:12][C:13]=1[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1-(5-ethyl-4-p-tolyl-thiophen-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one (18 mg, 48 μmol) in ethanol (1.5 mL) and 3 N aq. NaOH (0.3 mL) is treated with (S)-3-chloro-propane-1,2-diol (30 μL) and the mixture is stirred at 60° C. for 14 h. The solvent is removed in vacuo and the residue is separated on prep. TLC plates with heptane:EA 2:1 to give 3-[4-((S)-2,3-dihydroxy-propoxy)-3,5-dimethyl-phenyl]-1-(5-ethyl-4-o-tolyl-thiophen-2-yl)-propan-1-one (4 mg) as a colourless resin; LC-MS: tR=1.04 min, [M+1]+=453.28; 1H NMR (CDCl3): δ 7.45 (s, 1H), 7.92-7.08 (m, 4H), 6.87 (s, 2H), 4.11-4.04 (m, 1H), 3.87-3.80 (m, 4H), 3.16-3.10 (m, 2H), 2.97-2.90 (m, 2H), 2.64 (q, J=7.6 Hz, 2H), 2.24 (s, 3H), 2.17 (s, 6H), 1.20 (t, J=7.6 Hz, 3H).

Workup

customThe solvent is removed in vacuo
customthe residue is separated on prep

Sources & evidence

ORD record: ord-b19414e148b845828e673047450e1e0b
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951794B2

Reaction notes

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