Methanol → HCID 22908104, compound

HRID 1379791Notes

Reaction equation

HRID 1379791 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[C:7]([S:14][C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=3)=[CH:6][CH:5]=[CH:4][C:3]1=2.CC1(C)CCC(C)(C)C2C=C(SC3C=CC(C(OCC)=O)=CC=3)C=CC1=2.[Li+].[OH-].CO>O1CCCC1>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[C:7]([S:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:24][CH:25]=3)=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 10761557HCID 10761557, compoundHCID 22908100HCID 22908100, compound

Product 1

HCID 22908104HCID 22908104, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 70 mg (0.19 mmol) of ethyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthylthio)benzoate (Compound 1) in 4.0 mL of tetrahydrofuran was added 1.0 mL of LiOH (1.9N aqueous solution) and 1.5 mL of MeOH. The solution was heated at 55° C. for 3 h, cooled to room temperature and concentrated in vacuo. The residue was diluted with water and extracted with hexane. The aqueous layer was acidified to pH=l using 10% HCl and extracted twice with diethyl ether. The combined organic layers were washed with brine, dried (MgSO4), filtered and the solvents removed in vacuo. Purification of crude product by flash chromatography on silica gel (7:3/hexane:ethyl acetate) gave the title compound as a white solid (40 rag, 62%):

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with hexane
  5. extractionextracted twice with diethyl ether
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvents removed in vacuo
  10. customPurification of crude product by flash chromatography on silica gel (7:3/hexane:ethyl acetate)

Sources & evidence

ORD record
ord-c6c082bd692e42a5b4ffc87c5f335bb1
Source dataset
uspto-grants-1997_09
Patent number
US05672710

Reaction notes

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