Hydrochloric Acid → Spiro[4.5]dec-6-ene-7-methanol

HRID 2070550Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH2:14][CH2:13][CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=1)=O.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C(OCC)(=O)C>[CH2:11]1[C:7]2([CH2:12][CH2:13][CH2:14][C:5]([CH2:3][OH:2])=[CH:6]2)[CH2:8][CH2:9][CH2:10]1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of spiro[4.5]dec-6-ene-7-carboxylic acid methyl ester (3.50 g) obtained in Step 5 in tetrahydrofuran (70 mL) was added dropwise a 1M toluene solution of diisobutylaluminum hydride (54.6 mL) under argon atmosphere at −70° C. over 15 minutes, followed by stirring the reaction mixture at −70° C. for 2 hours. After raising the temperature up to −15° C., to the reaction mixture were added successively 2N aqueous hydrochloric acid solution (60 mL) and ethyl acetate (100 mL), followed by separation of the organic layer. 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)=3:97 to 15:85) to give spiro[4.5]dec-6-ene-7-methanol (2.375 g).

Workup

temperatureAfter raising the temperature up to −15° C.
customfollowed by separation of the organic layer
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)=3:97 to 15:85)

Sources & evidence

ORD record: ord-176372cde49046b995949839883f979f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299296B2

Reaction notes

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