Aluminium lithium hydride → 2,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol

HRID 65462

Reaction equation

HRID 65462 reaction equation
C([O:3][C:4](=O)[C:5]([CH3:26])=[CH:6][CH:7]=[C:8]([CH3:25])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH:13]=[CH:14][C:15]1[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]=1[CH3:23])C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:26][C:5](=[CH:6][CH:7]=[C:8]([CH3:25])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH:13]=[CH:14][C:15]1[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]=1[CH3:23])[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 541525652,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoic acid ethyl ester

Product 1

HCID 537496932,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoic acid ethyl ester (1.85 g, 5 mmol) in 25 ml of anhydrous THF is cooled to -10° C. and 0.19 g (5 mmol) of LAH is added in portions. The resulting mixture is stirred for 4 hours and quenched carefully with 0.4 ml of water. The mixture is suction-filtered and the residue thoroughly washed with ether. The combined filtrate and washings are dried (MgSO4) and evaporated under reduced pressure to give the crude product. Purification by HPLC (4% ethylacetate in hexane on silica gel column) gives the pure desired product.

Workup

  1. customquenched carefully with 0.4 ml of water
  2. filtrationThe mixture is suction-filtered
  3. washthe residue thoroughly washed with ether
  4. dry with materialThe combined filtrate and washings are dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give the crude product
  7. customPurification by HPLC (4% ethylacetate in hexane on silica gel column)

Sources & evidence

ORD record
ord-4febf2555cbb4d9ba4b4ee53cca4bd48
Source dataset
uspto-grants-1986_09
Patent number
US04614747

Linked notes

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