4-Methoxybenzenethiol → (+/-)-t-butyl (2R*,3R*)-2-hydroxymethyl-3-(4-methoxyphenylsulfanyl)-7-phenylheptanoate
Reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.[OH:15][CH2:16]/[C:17](=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C1COCC1>[OH:15][CH2:16][C@@H:17]([C@H:25]([S:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=1)[CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of n-butyl lithium in hexanes (0.6 mL, 1.4 mmol) is added slowly to a mixture of 4-methoxybenzenethiol (2 g, 14 mmol) in THF (10 mL) at 0° C. After 2 minutes a solution of t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoate (2.2 g, 7.59 mmol) in THF (7 mL) is added and the reaction is allowed to warm to room temperature. After 1 hours the reaction is concentrated in vacuo and the crude product is purified by column chromatography using gradient elution (silica, 15 to 30% ether in petroleum ether) to give (±)-t-butyl (2R*,3R*)-2-hydroxymethyl-3-(4-methoxyphenylsulfanyl)-7-phenylheptanoate (3 g, 92%): 1H NMR (300 MHz, CDCl3) δ 7.39-7.34 (m, 2H), 7.30-7.25 (m, 2H), 7.20-7.13 (m, 3H), 6.86-6.81 (m, 2H), 4.07-3.98 (m,1H), 3.93-3.86 (m, 1H), 3.80 (s, 3H), 3.26-3.19 (m, 1H), 2.67-2.60 (m, 1H), 2.58 (t, J=7.2 Hz, 2H), 2.38 (t, J=6.6 Hz, 1H), 1.65-1.47 (m, 6H), 1.46 (s, 9H); MS (FAB) m/e 430 (M+).
Workup
- concentrationAfter 1 hours the reaction is concentrated in vacuo
- customthe crude product is purified by column chromatography
- washelution (silica, 15 to 30% ether in petroleum ether)
Sources & evidence
- ORD record
- ord-aeb042864d064bcabfcf4c6eb9e707c8
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06057369
Reaction notes
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