Hexanal → HCID 15785703, compound

HRID 440322Notes

Reaction equation

HRID 440322 reaction equation
[Li]CCCC.Br[C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[CH:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].CC([Si](Cl)(C)C)(C)C>CCOCC>[OH:18][CH:12]([C:7]1[S:8][CH:9]=[CH:10][N:11]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6184HexanalHCID 28928tert-Butyldimethylsilyl chlorideHCID 764302-BromothiazoleHCID 178418339Butyllithium

Product 1

HCID 15785703HCID 15785703, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-BuLi (4.0 mL, 6.4 mmol, 1.6M) was added dropwise to a -78° C. solution of 2-bromothiazole (1.0 g, 6.1 mmol) in dry Et2O (12 mL). After stirring at -78° C. for 1 h, hexanal (0.77 mL, 6.4 mmol) was added and the solution stirred for 30 min. before a solution of TBDMSCl (1.1 g, 7.3 mmol) in dry Et2O (5 mL) was added. The solution was allowed to warm to rt while stirring for 16 h. The reaction was quenched with water, the layers separated and the aqueous extracted with EtOAc. The combined extracts were dried (MgSO4) and condensed. The crude material was purified by flash chromatography using 30% EtOAc/hexane to give 0.70 g (62%) of 2-(1-hydroxyhexyl)thiazole.

Workup

  1. additionwas added
  2. temperatureto warm to rt
  3. stirringwhile stirring for 16 h
  4. customThe reaction was quenched with water
  5. customthe layers separated
  6. extractionthe aqueous extracted with EtOAc
  7. customThe combined extracts were dried
  8. custom(MgSO4) and condensed
  9. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-f6dba65653d9417194b391d6fb91049a
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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