Allylbenzene → HCID 67378154, compound

HRID 1909499Notes

Reaction equation

HRID 1909499 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[CH:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1)=C>>[CH3:10][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]/[CH:3]=[CH:2]\[CH2:1][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 9309AllylbenzeneHCID 11159402HCID 11159402, compound

Product 1

HCID 67378154HCID 67378154, compoundYield 56%

Procedure

Following the general procedure, allyl benzene (50.0 mg, 0.423 mmol, 7) was treated with p-methoxyphenyl vinyl ether (127 mg, 8.46 mmol) and 1.2 mol % of in situ-generated complex la (51.0 μL, 0.10 M, 5.08 μmol; final substrate concentration=8.3 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 10a (56.8 mg, 0.236 mmol, 56.0% yield, >98% Z isomer) as a colorless oil. IR (neat): 3027 (w), 3000 (w), 2950 (w), 2908 (w), 2834 (w), 1664 (m), 1502 (s), 1464 (m), 1453 (m), 1441 (m), 1384 (m), 1212 (s), 1179 (m), 1088 (m), 1064 (m), 1034 (m), 989 (m); NMR (400 MHz, CDCl3): δ 7.33-7.25 (4H, m), 7.24-7.18 (1H, m), 7.01-6.95 (2H, m), 6.89-6.84 (2H, m), 6.42 (1H, dt, J=6.0, 1.6 Hz), 4.96 (1H, td, J=7.6, 6.0 Hz), 3.80 (3H, s), 3.58 (2H, dd, J=7.6, 1.2 Hz); 13C NMR (100 MHz, CDCl3): δ 155.4, 151.7, 141.9, 141.2, 128.6, 128.5, 126.0, 117.6, 114.8, 110.6, 55.9, 30.4; HRMS (ESI+) [M+NH4]+ calcd for C16H20NO2. 258.1494, found: 258.1491.

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-d1cdc2df33b8420bb87803550e7439a2
Source dataset
uspto-grants-2013_12
Patent number
US08598400B2

Reaction notes

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