Imidazole → 1-Butylcyclobutanecarboxylic Acid
Reaction equation
[CH2:1]([C:5]1([CH:9]([OH:12])C#C)[CH2:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].N1C=CN=C1.[Si](Cl)(C(C)(C)C)(C)C.CN(C=[O:30])C>>[CH2:1]([C:5]1([C:9]([OH:12])=[O:30])[CH2:6][CH2:7][CH2:8]1)[CH2:2][CH2:3][CH3:4]Participants
5
Procedure
To 6.26 g (37.6 mmol) of crude 1-(1-butylcyclobutyl)prop-2-yn-1-ol in DMF (20 mL) were added imidazole (3.1 g, 45.2 mmol) and tert-butyldimethylsilyl chloride (6.8 g, 45.2 mmol). The reaction mixture was stirred at RT overnight, then concentrated to remove DMF, diluted with 100 ml of EtOAc, and added 100 mL of sat. aq. NH4Cl. After separation, the aq. phase was extracted with EtOAc (2×100 mL). The combined organic phase was washed with 50 mL of brine, dried (Na2SO4), concentrated. Flash chromatography over silica gel of the crude product (eluted with hexanes) afforded the title intermediate (6.82 g, 58% 3 steps) as colorless oil.
Workup
- concentrationconcentrated
- customto remove DMF
- additiondiluted with 100 ml of EtOAc
- additionadded 100 mL of sat. aq. NH4Cl
- customAfter separation
- extractionthe aq. phase was extracted with EtOAc (2×100 mL)
- washThe combined organic phase was washed with 50 mL of brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0ec414a7fd8747b79056604ccda9b980
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07335680B2
Reaction notes
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