Methanol → HCID 178490207, compound

HRID 1028925Notes

Reaction equation

HRID 1028925 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:12][CH2:13][C:14]([OH:16])=[S:15])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CO.O>O1CCCC1.C(OCC)(=O)C.C(Cl)(Cl)Cl>[OH:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:12][CH2:13][C:14]([OH:16])=[S:15]

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 178490209HCID 178490209, compound

Product 1

HCID 178490207HCID 178490207, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a cooled solution of 3-[(tert-Butyldimethylsilyl)oxy]-4-methoxybenzylthio acetic acid 16 (8.75 g, 25.5 mmol) in tetrahydrofuran (40 mL) was added 1.0 M solution of tetra-n-butyl ammonium fluoride in tetrahydrofuran (6.68 g or 25.54 mL, 25.5 mmol) slowly and stirred under nitrogen for 2 h at room temperature. The progress of the reaction was monitored by TLC (9:1—chloroform:methanol on silica gel plate). Water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with water and dried. Removal of the solvent in vacuo yielded a semi solid that was subjected to column chromatography (initial with chloroform and finally with ethyl acetate) afforded the pure product 17. Yield: 50%; white solid mp 128-130° C. 1H NMR: δ 3.34 (s, 2H, CH2), 3.84 (s, 3H, OCH3), 4.04 (s, 2H, CH2), 6.80-7.01 (m, 3H, Ar—H). Anal. Calcd for C10H12O4S: C, 52.62, H, 5.30. Found: C, 52.58, H, 5.35.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customRemoval of the solvent in vacuo
  5. customyielded a semi solid

Sources & evidence

ORD record
ord-e811c755e9d6426592e4e91cd59ebea9
Source dataset
uspto-grants-2014_05
Patent number
US08735620B2

Reaction notes

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