Toluene → HCID 67483437, compound

HRID 324879Notes

Reaction equation

HRID 324879 reaction equation
C([C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:6]([CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:5]([CH:40]([CH3:42])[CH3:41])[N:4]=1)=O.C1(P(=[CH:62][C:63]([O:65][CH3:66])=[O:64])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:67]1(C)C=CC=CC=1>>[C:63]([CH:62]=[CH:67][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:7]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[C:6]([CH2:21][O:22][Si:23]([C:36]([CH3:38])([CH3:39])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:5]([CH:40]([CH3:41])[CH3:42])[N:4]=1)([O:65][CH3:66])=[O:64]

Participants

4

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 22005162HCID 22005162, compound

Product 1

HCID 67483437HCID 67483437, compound

Procedure

A mixture of the intermediate obtained in Example 205, Step A (50 mg, 85 mmol) and methyl (triphenylphosphoranylidene)acetate (31 mg, 1.1 equiv) in toluene (5 mL) was heated to reflux for 5 h. The mixture was cooled to rt and concentrated in vacuo. Silica gel chromatography provided a yellow oil (60 mg). 1H NMR (CDCl3, 300 MHz): δ 7.96 (d, 15.1 Hz, 1H), 7.42 (m, 6H), 7.34-7.21 (m, 5H), 7.05 (s, 2H), 7.03 (s, 2H), 4.28 (s, 2H), 3.84 (s, 3H), 3.17 (sept, 6.8 Hz, 1H), 2.38 (m, 2H), 1.31 (m, 2H), 1.19 (d, 6.6 Hz, 6H), 1.14 (m, 4H), 1.00 (s, 9H), 0.79 (t, 6.6 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26df374ae75c4ef598beed79a2010c43
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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