Hydrochloric Acid → HCID 57771562, compound

HRID 2070612Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:13][CH2:12][CH2:11][CH2:10][C:7]2([CH2:9][CH2:8]2)[CH:6]1OC(=O)C)=O.N12CCCN=C1CCCCC2.O.Cl>C1(C)C=CC=CC=1>[CH2:9]1[C:7]2([CH2:10][CH2:11][CH2:12][CH2:13][C:5]([CH2:3][OH:2])=[CH:6]2)[CH2:8]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-acetoxy-spiro[2.6]nonane-5-carboxylic acid methyl ester (1.06 g) obtained in Step 3 in toluene (11 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (3.3 mL), followed by stirring the reaction mixture at 120° C. for 5.5 hours. After ice-cooling the reaction mixture, water (25 mL) and 1N aqueous hydrochloric acid solution (25 mL) were added thereto, followed by extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (diethyl ether:hexane (volume ratio)=1:20) to give spiro[2.6]non-4-en-5-yl-methanol (0.32 g).

Workup

additionwere added
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (diethyl ether:hexane (volume ratio)=1:20)

Sources & evidence

ORD record: ord-a4bc05b53ae7476a98a5af1fee22c4db
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299296B2

Reaction notes

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