Acetic Acid → t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoate

HRID 1107175Notes

Reaction equation

C([O:9][CH2:10]/[C:11](/[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[OH:9][CH2:10]/[C:11](=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)/[C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

(E)-2-t-Butoxycarbonyl-7-phenylhept-2-enyl benzoate (5.9 g, 15 mmol) is dissolved in MeOH (75 mL) and cooled to 0° C. K2CO3 (2 g, 15 mmol) is added with stirring and the reaction is allowed to warm to 23° C. After 2 hours the reaction is neutralized with HOAc and the reaction is concentrated to approximately half of its volume. After diluting with ether (500 mL), the solution is washed with water (50 mL) and brine (50 mL). The resulting solution is dried (MgSO4) and concentrated in vacuo. The crude reaction mixture is purified by column chromatography (silica, 25% ether in petroleum ether) to give t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoate (2.2 g, 51%): 1H NMR (300 MHz, CDCl3) δ 7.30-7.25 (m, 2H), 7.20-7.15 (m, 3H), 6.75 (t, J=7.7 Hz, 1H), 4.28 (d, J=6.8 Hz, 2H), 2.65-2.60 (m, 3H), 2.26 (q, J=7.5 Hz, 2H), 1.71-1.61 (m, 2H), 1.53-1.43 (m, 11H).

Workup

temperatureto warm to 23° C
concentrationthe reaction is concentrated to approximately half of its volume
additionAfter diluting with ether (500 mL)
washthe solution is washed with water (50 mL) and brine (50 mL)
dry with materialThe resulting solution is dried (MgSO4)
concentrationconcentrated in vacuo
customThe crude reaction mixture
customis purified by column chromatography (silica, 25% ether in petroleum ether)

Sources & evidence

ORD record: ord-f7a879bc6a8847aa9e9f30d2f6deb0d2
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057369

Reaction notes

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