Water → 3-[1-Hydroxy-1-(thiazol-2-yl)propyl]phenol
Reaction equation
[OH:1][C:2]([C:10]1[CH:11]=[C:12]([O:16][Si](C(C)(C)C)(C)C)[CH:13]=[CH:14][CH:15]=1)([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)[CH2:3][CH3:4].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[OH:1][C:2]([C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)[CH2:3][CH3:4]Participants
5
Procedure
To a solution of compound from Step 2 (5.57 g, 15.96 mmol) in THF (40 mL) there was added n-Bu4NF 1M in THF (18 mL); the mixture was stirred at r.t. for 30 min., then H2O (10 mL) was added. The mixture was concentrated to a small volume, the residue extracted with EtOAc, the extract washed twice with brine, dried and evaporated to a residue which was chromatographed on silica gel, eluting with a 1:1 mixture of EtOAc and hexane, to afford the title product as a white solid (2.59 g) m.p. 145°-146° C.
Workup
- concentrationThe mixture was concentrated to a small volume
- extractionthe residue extracted with EtOAc
- washthe extract washed twice with brine
- customdried
- customevaporated to a residue which
- customwas chromatographed on silica gel
- washeluting with a 1:1 mixture of EtOAc and hexane
Sources & evidence
- ORD record
- ord-e446bef0b2164bcdaa90f173ed33be66
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05527827
Reaction notes
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