Hydrochloric Acid → Methyl 7-phenyl-3,5-dihydroxy-6-heptenoate

HRID 2226276

Reaction equation

HRID 2226276 reaction equation
[C:1]1([CH:7]=[CH:8][CH:9]([OH:18])[CH2:10][C:11](=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].O.Cl>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].[Cl-].[Ti+4]>[C:1]1([CH:7]=[CH:8][CH:9]([OH:18])[CH2:10][CH:11]([OH:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 53740643Methyl 7-phenyl-5-hydroxy-3-oxo-6-heptenoate

Product 1

HCID 54384934Methyl 7-phenyl-3,5-dihydroxy-6-heptenoateYield 65.2%

Reagents, catalysts & solvents 2

HCID 3084342Chlorotitanium triisopropoxideCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

700 mg of methyl 7-phenyl-5-hydroxy-3-oxo-6-heptenoate (2.82 mmol) are dissolved in 25 cm3 of methanol and then cooled to -10° C. 0.71 cm3 of titanium chloride triisopropoxide (2.82 mmol) is added. The mixture is stirred for 20 minutes at -10° C. 207.8 mg of sodium cyanoborohydride (3.1 mmol) are then added and the mixture is then stirred for 3 hours 45 minutes at a temperature between -5° and 0° C. 5 cm3 of water and 1 cm3 of concentrated hydrochloric acid are added. After evaporation of the methanol under reduced pressure, the mixture is taken up in 50 cm3 of dichloromethane. The organic phase is washed with 25 cm3 of a saturated sodium bicarbonate solution and then with 25 cm3 of water and is then dried over sodium sulphate. After filtration and concentration to dryness, the residue obtained is treated with methanol. There is thus obtained, with a yield of 55%, 460 mg of methyl 7-phenyl-3,5-dihydroxy-6-heptenoate for which the syn/anti ratio is equal to 80/20.

Workup

  1. stirringthe mixture is then stirred for 3 hours 45 minutes at a temperature between -5° and 0° C
  2. customAfter evaporation of the methanol under reduced pressure
  3. washThe organic phase is washed with 25 cm3 of a saturated sodium bicarbonate solution
  4. dry with materialwith 25 cm3 of water and is then dried over sodium sulphate
  5. filtrationAfter filtration and concentration to dryness
  6. customthe residue obtained

Sources & evidence

ORD record
ord-023e42b75a2240e9b7673525036c317b
Source dataset
uspto-grants-1994_09
Patent number
US05347039

Linked notes

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