Ethyl cinnamyl carbonate → 1-Phenyl-1-phenoxy-2-propene

HRID 14441Notes

Reaction equation

HRID 14441 reaction equation
[O-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].C(=O)(O[CH2:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)OCC>>[C:17]1([CH:16]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH2:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 232463Ethyl cinnamyl carbonateHCID 4445035Phenolate Sodium

Product 1

HCID 117359621-Phenyl-1-phenoxy-2-propeneYield 81.3%

Procedure

By the procedure for entry 9 of Table 1, the reaction of sodium phenoxide (232 mg, 2.00 mmol) and ethyl cinnamyl carbonate (192 mg, 0.930 mmol) with [(COD)IrCl]2 (6.7 mg, 0.010 mmol) and L1 (Sa,Sc,Sc) (10.8 mg, 0.0200 mmol) as catalyst was conducted at room temperature for 32 h. 1H NMR analysis of the crude reaction showed the ratios of branched to linear products to be 99/1. After purification, 159 mg of the title compound (75%) was isolated. HPLC analysis as described above indicated that the enantiomeric excess of the major product was 94%.

Workup

  1. custom1H NMR analysis of the crude reaction
  2. customAfter purification

Sources & evidence

ORD record
ord-cc18da941b554ad5b0897d3daa0d8ff2
Source dataset
uspto-grants-2010_06
Patent number
US07732365B2

Reaction notes

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