Methanol → HCID 86751362, compound

HRID 1379793Notes

Reaction equation

HRID 1379793 reaction equation
[CH3:1][C:2]1[C:3]([O:16][S:17](=[O:31])(=[O:30])[O:18][C:19]2[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[Li+].[OH-].CO>O1CCCC1>[CH3:1][C:2]1[C:3]([O:16][S:17](=[O:31])(=[O:30])[O:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][CH:29]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86751363HCID 86751363, compound2×

Product 1

HCID 86751362HCID 86751362, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 58 mg (0.15 mmol) of ethyl 4-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthylsulfoxy)benzoate (Compound 8) in 4.0 mL of tetrahydrofuran was added 1.0 mL of LiOH (2N aqueous solution) and 2.0 ml of MeOH. The solution was heated at 55° C. for 2 h and stirred at room temperature for 8 h. The reaction mixture was then concentrated in vacuo. The residue was diluted with brine and 10% HCl and extracted with diethyl ether (2×). The combined ether layers were dried (MgSO4), filtered, and the solvents removed in vacuo to give the title compound as a white solid (0.39 mg, 72%):

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionThe residue was diluted with brine and 10% HCl
  3. extractionextracted with diethyl ether (2×)
  4. dry with materialThe combined ether layers were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-abb3ed4db4c3491b93408dac73b84038
Source dataset
uspto-grants-1997_09
Patent number
US05672710

Reaction notes

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