Methanol → HCID 9820836, compound

HRID 1379792Notes

Reaction equation

HRID 1379792 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([S:14]([C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:5]=[CH:4][C:3]1=2.[Li+].[OH-].CO>O1CCCC1>[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([S:14]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:26][CH:27]=3)(=[O:16])=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 15285890HCID 15285890, compound2×

Product 1

HCID 9820836HCID 9820836, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 95 mg (0.23 mmol) of ethyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylsulfonyl)benzoate (Compound 4) in 4.0 mL of tetrahydrofuran was added 1.0 mL of LiOH (2.6N aqueous solution) and 1.4 mL of MeOH. The solution was heated at 55° C. for 2.5 h, cooled to room temperature and concentrated in vacuo. The residue was diluted with brine, acidified to pH=1 using 10% HCl and extracted with ether (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and the solvents were removed in vacuo to give the title compound as a white solid (80 mg, 91%):

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with brine
  4. extractionextracted with ether (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-3a71a0eb6de144f0b00c4cd4d6ba7659
Source dataset
uspto-grants-1997_09
Patent number
US05672710

Reaction notes

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