Ethanol → HCID 57771448, compound

HRID 2070566Notes

Reaction equation

HRID 2070566 reaction equation
[CH2:1]1[C:5]2([CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][CH:2]1[CH2:12][OH:13].C(O)C.[H][H]>O1CCCC1.[C].[Pd]>[CH2:1]1[C:5]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][CH:2]1[CH2:12][OH:13]

Participants

6

Reactant 3

HCID 702EthanolHCID 57771615HCID 57771615, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57771448HCID 57771448, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of spiro[4.6]undec-8-ene-2-methanol (44 mg) obtained in Step 6 and 5% palladium carbon (4 mg) in tetrahydrofuran (1 mL)-ethanol (1 mL) was stirred in an atmosphere of hydrogen for 3 hours. Then, the reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by column chromatography on silica gel to give spiro[4.6]undecane-2-methanol (43 mg).

Workup

  1. filtrationThen, the reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-10de776a9c8d484aa96062d24b3da0fb
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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