Hydrochloric Acid → HCID 57771486, compound

HRID 2070570Notes

Reaction equation

HRID 2070570 reaction equation
C([O:3][C:4]([C:6]1[CH2:15][CH2:14][C:9]2([CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:8][CH:7]=1)=O)C.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[CH2:13]1[C:9]2([CH2:14][CH2:15][C:6]([CH2:4][OH:3])=[CH:7][CH2:8]2)[CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 57771539HCID 57771539, compound

Product 1

HCID 57771486HCID 57771486, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of spiro[4.5]dec-7-ene-8-carboxylic acid ethyl ester (2.8 g) obtained in Step 3 in tetrahydrofuran (40 mL) was added dropwise a toluene solution of diisobutylaluminum hydride (0.99 M, 41 mL) under argon atmosphere at −78° C., followed by stirring the reaction mixture at −78° C. for 1 hour. Then, after adding 2N aqueous hydrochloric acid solution and raising the temperature to room temperature, the reaction mixture was extracted with ethyl acetate twice. 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)=1:4) to give spiro[4.5]dec-7-en-8-yl-methanol (1.95 g).

Workup

  1. temperatureraising the temperature to room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate twice
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:4)

Sources & evidence

ORD record
ord-4ab9d35e75f44500b71e58c4a1c723c5
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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