8-Bromooct-1-ene → HCID 58460828, compound

HRID 1909500Notes

Reaction equation

HRID 1909500 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].[CH:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1)=C>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH3:10])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 759078-Bromooct-1-eneHCID 11159402HCID 11159402, compound

Product 1

HCID 58460828HCID 58460828, compoundYield 69.5%

Procedure

Following the general procedure, 8-bromooct-1-ene (50.0 mg, 0.262 mmol) was treated with p-methoxyphenyl vinyl ether (79.0 mg, 0.5 23 mmol) and 1.2 mol % of in situ-generated complex 1a (31.0 μL, 0.10 M, 3.14 μmol; final substrate concentration=8.45 M) and allowed to stir for 16 h. The unpurified product is >98% Z (as determined by 400 MHz 1H NMR analysis). Excess p-methoxyphenyl vinyl ether was removed by vacuum distillation (1.0 torr, 80° C.). The resulting oil was purified by neutral alumina chromatography (100% hexanes to 100:1 hexanes:Et2O) to afford 10b (56.9 mg, 0.182 mmol, 69.0% yield, >98% Z isomer) as a colorless oil. IR (neat): 2924 (s), 2854 (m), 1665 (m), 1503 (s), 1463 (m), 1441 (m), 1389 (w), 1214 (s), 1180 (m), 1102 (m), 1040 (s); 1H NMR (400 MHz, CDCl3): δ 6.95-6.90 (2H, m), 6.86-6.82 (2H, m), 6.28 (1H, dt, J=6.0, 1.5 Hz), 4.73 (1H, td, J=7.4, 6.0 Hz), 3.78 (3H, s), 3.40 (2H, t, J=7.0 Hz), 2.24-2.17 (2H, m), 1.90-1.81 (2H, m), 1.49-1.32 (6H, m); 13C NMR (100 MHz, CDCl3): δ 155.2, 151.8, 141.4, 117.5, 114.8, 112.0, 55.8, 34.1, 33.0, 29.4, 28.4, 28.1, 23.9; HRMS (ESI+) [M+H]+ calcd for C15H22BrO2: 313.0803, found: 313.0800

Workup

  1. customExcess p-methoxyphenyl vinyl ether was removed by vacuum distillation (1.0 torr, 80° C.)
  2. customThe resulting oil was purified by neutral alumina chromatography (100% hexanes to 100:1 hexanes:Et2O)

Sources & evidence

ORD record
ord-ae56a7e84ef64613b36da31c0a6f9af1
Source dataset
uspto-grants-2013_12
Patent number
US08598400B2

Reaction notes

Loading…