Tetrahydrofuran → HCID 11579164, compound

HRID 2253421Notes

Reaction equation

HRID 2253421 reaction equation
[CH:1]1(/[C:7](/[CH3:14])=[CH:8]/[C:9](OCC)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[CH:1]1(/[C:7](/[CH3:14])=[CH:8]/[CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9855836Potassium sodium tartarateHCID 12550542HCID 12550542, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11579164HCID 11579164, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a 0° C. solution of (E)-ethyl 3-cyclohexylbut-2-enoate (Appella et al. (1999), J. Am. Chem. Soc. 121:9473) (1 g, 5.09 mmol) in dry Et2O (10 mL) was added a solution of lithium aluminum hydride (5.10 mL, 5.10 mmol, 1 M in Et2O). After 5 minutes, the reaction mixture was neutralized by dropwise addition of THF solution followed by addition of a saturated solution of potassium sodium tartrate. The reaction mixture was stirred for 25 minutes, and then diluted with Et2O. The organic layer was separated and washed with water, dried over Na2SO4 and concentrated in vacuo to afford (E)-3-cyclohexylbut-2-en-1-ol as a colorless oil which was used directly in the following reaction.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6121330e33b546c393d54fa96920553b
Source dataset
uspto-grants-2008_01
Patent number
US07323604B2

Reaction notes

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