Toluene → HCID 10856208, compound

HRID 1357312Notes

Reaction equation

HRID 1357312 reaction equation
[CH2:1]([O:4][C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:7]#[CH:8])[CH3:6])[CH:2]=C.F[P-](F)(F)(F)(F)F.[C:22]1(C)C=CC=CC=1>>[CH3:6][C:5]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:7]([CH:8]=[CH2:22])=[CH:2][CH2:1][O:4]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 9886HexafluorophosphateHCID 110086362-allyloxy-2-phenylbut-3-yne

Product 1

HCID 10856208HCID 10856208, compound

Procedure

A solution of 2-allyloxy-2-phenylbut-3-yne (368 mg, 1.97 mmol) and the allenylidene complex (p-cymene)RuCl(PCy3)(═C═C═CPh2)+PF6− (43 mg, 0.0485 mmol, 2.5 mol %) in toluene (10 ml) is stirred for 24 hours at 80° C. under nitrogen. The solvent is evaporated and the crude product is purified by flash chromatography using ether:pentane (1:10) as the eluent. The title compound was obtained as a yellowish liquid (283 mg, 77%). 1H NMR (200 MHz, CDCl3): d=1.79 (s, 3H, CH3); 4.76 (m, 2H, J=0.8, OCH2); 5.02 (d, 1H, J=11.2, ═CH2); 5.06 (d, 1H, J=17.8, ═CH2); 5.98 (m, 1H, C═CH); 6.21 (ddd, 1H, J=17.8, 11.2 and 0.8, ═CH); 7.20-7.47 (m, 5H, Ph). 13C NMR (50 MHz, CDCl3): d=24.4 (CH3); 73.1 (OCH2); 89.8 (C); 117.1 (═CH2); 124.3 (═CH); 126.1 (Ph); 128.3. (═CH); 128.6, 128.9 (Ph); 144.5 (C); 144.7 (C Ph). IR (NaCl windows): 3088, 3060, 3029, 2979, 2832, 2837, 1821, 1644, 1620, 1596, 1492, 1448,1370, 1344, 1239, 1201, 1139, 1068, 1021, 991, 913, 865, 807, 763, 701. MS (rel. Intensity): 186 ([M+], 8); 172 (19); 171 (100); 153 (15); 144 (7); 143 (43); 142 (19); 128 (50); 127 (11); 115 (27); 109 (19); 105 (23); 91 (20); 81 (12); 79 (14); 78 (11); 77 (54); 76 (7); 66 (15); 65 (26); 63 (13); 55 (13); 53 (10); 52 (7); 51 (33); 50 (9); 43 (49); 40 (12); 39 (30); 27 (11). C13H14O (186.27): calcd. C, 83.83, H, 7.66; found: C, 83.54, H, 7.58.

Workup

  1. customThe solvent is evaporated
  2. customthe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-6375b672c13144368fa5df20e2698da5
Source dataset
uspto-grants-2003_07
Patent number
US06590048B1

Reaction notes

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