Hydrochloric Acid → Spiro[5.5]undec-1-ene-2-methanol
Reaction equation
C[O:2][C:3]([C:5]1[CH2:10][CH2:9][CH2:8][C:7]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=1)=O.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.[Cl-].[Na+].O.CO>[CH:6]1[C:7]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:8][CH2:9][CH2:10][C:5]=1[CH2:3][OH:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -70 °C
Procedure
To a solution of spiro[5.5]undec-1-ene-2-carboxylic acid methyl ester (2.07 g) obtained in Step 4 in tetrahydrofuran (30 mL) was added dropwise a 1M toluene solution of diisobutylaluminum hydride (30 mL) at −70° C. under argon atmosphere over 15 minutes, followed by stirring the reaction mixture at −70° C. for 1 hour. Then after careful addition of methanol (2 mL) and 6N aqueous hydrochloric acid solution (5 mL) to the reaction mixture, the temperature was raised to room temperature. The reaction mixture was poured into saturated brine, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:5) to give spiro[5.5]undec-1-ene-2-methanol (1.685 g).
Workup
- temperaturethe temperature was raised to room temperature
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with saturated brine
- customdried
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:5)
Sources & evidence
- ORD record
- ord-c3bc6a26bcee471484d66f21d0a289ac
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299296B2
Reaction notes
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