Alpha-Methylstyrene → HCID 11052785, compound

HRID 1089350Notes

Reaction equation

HRID 1089350 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[O:12]>C(=O)([O-])O.[Na+]>[OH:12][C@H:11]([CH2:3][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:1])[C:10]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 7407Alpha-MethylstyreneHCID 70205Acetic acid, 2-oxo-, methyl ester

Product 1

HCID 11052785HCID 11052785, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of an (R)-binaphthol-dichlorotitanium complex which had been prepared in the same manner as in Example 1 was cooled to -30° C. and added with 118 mg (1 mmole) of α-methylstyrene and 88 mg (1 mmole) of methyl glyoxylate, followed by reaction for 15 hours. Then, 10 ml of an aqueous sodium hydrogen-carbonate solution was added to terminate the reaction. The reaction mixture was filtered through Celite and extracted with two 20 ml portions of diethyl ether and two 20 ml portions of ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. Thereafter, the solvents were distilled off, and hexane was added to the residue to crystallize binaphthol. The remaining solution was purified by means of silica gel column chromatography to obtain 200 mg of methyl (R)-2-hydroxy-4-phenyl-4-pentenoate. The yield was 97%.

Workup

  1. customA solution of an (R)-binaphthol-dichlorotitanium complex which had been prepared in the same manner as in Example 1
  2. customfollowed by reaction for 15 hours
  3. customto terminate
  4. customthe reaction
  5. filtrationThe reaction mixture was filtered through Celite
  6. extractionextracted with two 20 ml portions of diethyl ether and two 20 ml portions of ethyl acetate
  7. dry with materialthe extract was dried over anhydrous magnesium sulfate
  8. distillationThereafter, the solvents were distilled off
  9. additionhexane was added to the residue
  10. customto crystallize binaphthol
  11. customThe remaining solution was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-8613ae5740414a8d97cbd6b17e83e1f9
Source dataset
uspto-grants-1990_10
Patent number
US04965398

Reaction notes

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