Vinylcyclohexane → HCID 67364419, compound

HRID 1909501Notes

Reaction equation

HRID 1909501 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH2:2].[CH:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=1)=C>>[CH:3]1(/[CH:1]=[CH:2]\[O:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:9])=[CH:13][CH:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 12757VinylcyclohexaneHCID 11159402HCID 11159402, compound

Product 1

HCID 67364419HCID 67364419, compoundYield 75.3%

Procedure

Following the general procedure, vinylcyclohexane (20.0 mg, 0.182 mmol) was treated with p-methoxyphenyl vinyl ether (55.0 mg, 0.363 mmol) and 5 mol % of in situ-generated complex 1a (91.0 μL, 0.10 M, 9.08 μmol; final substrate concentration=2.0 M) and allowed to stir for 24 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 (50:1 hexanes:Et2O) to afford 10d (31.8 mg, 0.137 mmol, 75.0% yield, >98% Z isomer) as a colorless oil. IR (neat): 2925 (m), 2850 (m), 1664 (w), 1505 (s), 1465 (w), 1447 (w), 1392 (w), 1293 (w), 1244 (m), 1224 (s), 1180 (w), 1102 (w), 1040 (m); 1H NMR (400 MHz, CDCl3): δ 6.95-6:91 (2H, m), 6.86-6.82 (2H, m), 6.17 (1H, dd, J=6.4, 1.2 Hz), 4.63 (1H, d, J=9.2, 6.0 Hz), 3.78 Hz (3H, s), 2.65-2.54 (1H, m), 1.78-1.60 (5H, m), 1.39-1.06 (5H, m); 13C NMR (100 MHz, CDCl3): δ 155.2, 151.9, 139.8, 118.6, 117.5, 114.8, 55.9, 33.6, 33.5, 26.3, 26.1; HRMS (ESI+) [M+H]+ calcd for C15H21O2: 233.1542, found: 233.1542.

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 (50:1 hexanes:Et2O)

Sources & evidence

ORD record
ord-b9af02c7837f4cf9915b2b17773f6703
Source dataset
uspto-grants-2013_12
Patent number
US08598400B2

Reaction notes

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