tert-Butyl acrylate → HCID 90408932, compound

HRID 1855036Notes

Reaction equation

HRID 1855036 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][OH:23])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH:25]=[CH2:26]>CO.C1(C)C=CC=CC=1>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][O:23][CH2:26][CH2:25][C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 15458tert-Butyl acrylateHCID 90409451HCID 90409451, compound

Product 1

HCID 90408932HCID 90408932, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methanol (50 mg, 0.161 mmol), tert-butyl acrylate (0.059 mL, 0.403 mmol), and Triton B (40% in MeOH) (7 μL, 0.016 mmol) in toluene (1 mL) was stirred at rt for 5 h. The mixture was concentrated in vacuo and the residue was purified by flash chromatography on SiO2 (0-30% EtOAc:hexanes) to afford the title compound (61 mg, 85% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 7.37-7.31 (m, 2H), 7.28 (dd, J=9.1, 6.7 Hz, 1H), 7.19-7.13 (m, 2H), 7.12-7.07 (m, 1H), 7.01 (ddd, J=4.4, 3.3, 1.8 Hz, 2H), 6.86 (ddd, J=8.0, 2.4, 1.0 Hz, 1H), 3.92 (s, 2H), 3.65 (t, J=6.3 Hz, 2H), 3.17 (s, 2H), 2.48 (t, J=6.3 Hz, 2H), 2.10-1.95 (m, 4H), 1.86-1.73 (m, 2H), 1.70-1.58 (m, 2H), 1.49 (s, 9H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography on SiO2 (0-30% EtOAc:hexanes)

Sources & evidence

ORD record
ord-80afec49389e418eaacdf01a39067381
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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