Ethylene → HCID 57835744, compound

HRID 1675286Notes

Reaction equation

HRID 1675286 reaction equation
C=C.[CH3:3][O:4][C:5]1[CH:36]=[CH:35][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH2:31][N+:32]([O-:34])=O)[CH2:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[O:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[C:37]1(N=C=O)C=CC=C[CH:38]=1>C1C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:36]=[CH:35][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH:17]([C:31]3[CH2:38][CH2:37][O:34][N:32]=3)[CH2:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[O:20])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6325EthyleneHCID 7672Phenyl isocyanateHCID 57835770HCID 57835770, compound

Product 1

HCID 57835744HCID 57835744, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethylene was bubbled into a mixture of 40.3 (235 mg, 0.5 mmol, see Example 40) in benzene (2 mL) for 20 minutes. Phenyl isocyanate (0.22 mL, 2 mmol) and TEA (3 drops) were then added. The mixture was stirred at room temperature for 2 days. The solid was removed by filtration and washed by benzene. The filtrate was concentrated and purified by flash chromatography to give 42.1 (200 mg). MS ESI (pos.) m/e: 476 (M+H). 1HNMR (CDCl3) δ 7.37 (d, 2H), 7.21 (d, 2H), 7.16 (d, 2H), 6.92 (m, 6H), 5.05 (dd, 2H), 4.98 (s, 2H), 4.25 (m, 2H), 4.10 (t, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.24 (dd, 1H), 2.79 (m, 3H).

Workup

  1. customThe solid was removed by filtration
  2. washwashed by benzene
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a4f0468dad484035bcc5aeb8e4f4a68d
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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