Hydrochloric Acid → HCID 67787613, compound

HRID 273763Notes

Reaction equation

HRID 273763 reaction equation
C([C:3]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]([OH:9])[CH2:7][CH2:6][CH2:5][C:4]1(CC)[CH:10]([C:14]([O-:16])=[O:15])[C:11]([O-:13])=[O:12])C.[OH-].[Na+].Cl>C1COCC1.O>[C:19]1([CH:3]2[CH:8]([OH:9])[CH2:7][CH2:6][CH2:5][CH:4]2[CH:10]([C:14]([OH:16])=[O:15])[C:11]([OH:13])=[O:12])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131718844HCID 131718844, compound

Product 1

HCID 67787613HCID 67787613, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 0.87 g (2.6 mmole) of diethyl-2-(SR)-phenyl-3-(SR)-hydroxy-(SR)-cyclohexylmalonate in 12 mL of THF and 7 mL of water was treated with 3.1 mL (7.8 mmole) of 10% aqueous sodium hydroxide and the mixture was heated in an oil bath at 70° C. under nitrogen for 24 hr. The mixture was cooled, 10 mL of water was added and the pH was adjusted to 2 with 2N aqueous HCl. The mixture was extracted with 3×35 mL of ethyl acetate, and the organic layer was dried with magnesium sulfate, filtered and concentrated in vacuo to give 700 mg of a light yellow foam. This material was carried on in Step F below.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with 3×35 mL of ethyl acetate
  3. dry with materialthe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffcad41a690c46caa4d9835e094ac018
Source dataset
uspto-grants-1995_02
Patent number
US05387595

Reaction notes

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