Water → HCID 23436666, compound

HRID 2120940Notes

Reaction equation

HRID 2120940 reaction equation
[C:1]12([C:8]3[C:12](=C)[CH:11]=[CH:10][CH:9]=3)[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(OCC)C>O1CCCC1>[C:1]12([C:8]3[CH2:12][CH:11]=[CH:10][CH:9]=3)[CH2:7][CH:4]([CH2:3][CH2:2]1)[CH2:5][CH2:6]2

Participants

6

Reactant 4

HCID 962Water2×HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 86588813Norbornylfulvene

Product 1

HCID 23436666HCID 23436666, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of norbornylfulvene (14.37 g, 90.8 mmol) dissolved in 100 mL tetrahydrofuran was cooled to 0° C. before LiAlH4 (5.00 g, 132 mmol) was added over 2 minutes. After stirring at room temperature for 17 hours, the reaction was cooled to 0° C. and 100 mL water were added dropwise over 1 hour. Then, 200 mL water/50 mL concentrated aqueous HCl and 100 mL diethyl ether were added. The organic layer was isolated and the aqueous layer was extracted with diethyl ether (3×50 mL). The organic layers were dried over MgSO4, filtered, and rotavapped to provide the crude product as a light yellow oil in quantitative yield.

Workup

  1. additionwas added over 2 minutes
  2. temperaturethe reaction was cooled to 0° C.
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with diethyl ether (3×50 mL)
  5. dry with materialThe organic layers were dried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b06bc63294f447a4830b8a92e20d55b0
Source dataset
uspto-grants-2004_02
Patent number
US06693153B2

Reaction notes

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