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Water → HCID 69017920, compound

HRID 1436335
Notes
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Reaction equation

HRID 1436335 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 962WaterHCID 69017589HCID 69017589, compound2×

Product 1

HCID 69017920HCID 69017920, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

30.4 mg (0.086 mmol) of 2-acetyloxy-2′-vinyloxy1,1′-binaphthyl and 2.8 mg (0.004 mmol) of Co (OAc) (L3) were dissolved in 90 μl of a mixed solvent (2:1) of methanol and THF under the atmosphere and 8 μl (0.44 mmol) of water was added to the mixture, and the mixture was then stirred at 0° C. After 10 hours, the reaction solution was analyzed by HPLC, to find that 66% of the 2-acetyloxy-2′-vinyloxy1,1′-binaphthyl was left with an optical purity of 44% ee. Further, the reaction solution was purified by silica gel column chromatography to obtain the reaction product O-acetylbinaphthol in a yield of 34%. Also, the kre1 value showing the selectivity of reactions at this time was 20.7.

Workup

  1. additionwas added to the mixture
  2. waitwas left with an optical purity of 44% ee
  3. customFurther, the reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7f2484cd238c46aa90a87e5b83e7cad9
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07619003B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes