Water → HCID 69017920, compound

HRID 1436336Notes

Reaction equation

HRID 1436336 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1OC=C)(=[O:3])[CH3:2].O>CO.C1COCC1>[C:1]([O:4][C:5]1[C:6]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[CH:10][CH:9]=[CH:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 69017589HCID 69017589, compound

Product 1

HCID 69017920HCID 69017920, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

95.8 mg (0.27 mmol) of 2-acetyloxy-2′-vinyloxy1,1′-binaphthyl and 9.0 mg (0.014 mmol) of Co(OAc) (L3) were dissolved in 0.27 ml of a mixed solvent (2:1) of methanol and THF under the atmosphere, 25 μl (1.44 mmol) of water was added to the mixture, and the mixture was then stirred at 0° C. After 21 hours, the reaction solution was purified by silica gel column chromatography and as a result, 34% of 2-acetyloxy-2′-vinyloxy-1,1′-binaphthyl was left with an optical purity of 86% ee measured by HPLC. The reaction product O-acetylbinaphthol was obtained in a yield of 66%. Also, the kre1 value showing the selectivity of reactions at this time was 6.6.

Workup

  1. additionwas added to the mixture
  2. customthe reaction solution was purified by silica gel column chromatography and as a result, 34% of 2-acetyloxy-2′-vinyloxy-1,1′-binaphthyl
  3. waitwas left with an optical purity of 86% ee

Sources & evidence

ORD record
ord-f3290f0fa4b54ba0b54fc1c09ca3edd0
Source dataset
uspto-grants-2009_11
Patent number
US07619003B2

Reaction notes

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