Sodium Thiosulfate Pentahydrate → methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

HRID 2425477Notes

Reaction equation

HRID 2425477 reaction equation
I[Si](C)(C)C.[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][O:20]C)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C.CO>[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][OH:20])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 4

HCID 61475Sodium Thiosulfate PentahydrateHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 59127146methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

Product 1

HCID 59127187methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Iodo-trimethyl-silane (CAS no. 16029-98-4) (115 mL, 0.79 mol) was added to a solution of methyl 3-hydroxy-5-[(2S)-1-methoxypropan-2-yl]oxy-benzoate (CAS no. 863504-77-2) (38.01 g, 0.158 mol) in acetonitrile (500 mL) and stirred for 24 hours. Methanol (300 mL) was added and the reaction stirred for 10 minutes. 10% w/v Aqueous sodium thiosulfate pentahydrate (100 mL) was added to the mixture and stirred for 20 minutes. The reaction mixture was neutralised with saturated aqueous sodium bicarbonate solution, the organic solvents removed in vacuo, and the product extracted into ethyl acetate (4×100 mL). The combined organic layers were dried (MgSO4), filtered and the solvents removed in vacuo. The crude material was crystallised from ethyl acetate to give the desired compound (16.8 g).

Workup

  1. additionwas added to the mixture
  2. stirringstirred for 20 minutes
  3. customthe organic solvents removed in vacuo
  4. extractionthe product extracted into ethyl acetate (4×100 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents removed in vacuo
  8. customThe crude material was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-eee19a38c4f343bea80ce8b71fffd811
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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