반응 #48802

반응 방정식

sodium bicarbonate

Trimethylsilyl iodide

methyl 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]benzoate

sodium thiosulfate pentahydrate

→

title compound

수율 47.0%

Methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

수율 47.0%

용매

acetonitrile

Methanol

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction stirred for 10 mins
2. 2
   workup.ADDITIONwas added to the mixture
3. 3
   workup.STIRRINGstirred for 20 mins
4. 4
   기타the organic solvents removed in vacuo
5. 5
   추출the product extracted into ethyl acetate (4×100 mL)
6. 6
   건조The combined organic layers were dried (MgSO4)
7. 7
   여과filtered
8. 8
   기타the solvents removed in vacuo
9. 9
   기타The crude material was crystallised from ethyl acetate

실험 절차

Trimethylsilyl iodide (115 mL, 0.79 mol) was added to a solution of methyl 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]benzoate (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 mins. 10% w/v Aqueous sodium thiosulfate pentahydrate (100 mL) was added to the mixture and stirred for 20 mins. 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 title compound (16.80 g)

출처