Bexarotene → {4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl}-methanol

HRID 2100687Notes

Reaction equation

HRID 2100687 reaction equation
[CH3:1][C:2]1[C:3]([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)=[CH2:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[C:3]([C:16]([C:18]2[CH:26]=[CH:25][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=2)=[CH2:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 82146BexaroteneHCID 21226445Aluminium lithium hydride

Product 1

HCID 57799975{4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl}-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid in 10 mL of THF was added 300 mg of LiAlH4 at 0° C. The mixture was stirred at room temperature overnight. The excess LiAlH4 was quenched with EtOAc (3 mL). The mixture was stirred for 30 min. 1N HCl was added. A sequence of extraction with EtOAc, filtering, concentration in vacuo and column chromatography yielded 180 mg of the desired alcohol and 103 mg of its acetate. The acetate formed was dissolved in 2 mL of THF, 1 mL of MeOH and 1 mL of H2O. NaOH (0.2 mL of a 1N solution, 0.2 mmol) was added. The mixture was stirred at room temperature for 1 hour. NH4Cl solution was added, and the alcohol product was extracted with EtOAc. After drying over MgSO4, filtering, concentration in vacuo and chromatography, 73.5 mg of the alcohol product was obtained. Total yield of the alcohol was therefore 253.5 mg.

Workup

  1. customThe excess LiAlH4 was quenched with EtOAc (3 mL)
  2. stirringThe mixture was stirred for 30 min
  3. addition1N HCl was added
  4. extractionA sequence of extraction with EtOAc
  5. filtrationfiltering
  6. concentrationconcentration in vacuo and column chromatography

Sources & evidence

ORD record
ord-ff483d013ed2495ba5f3a06e24c6c97f
Source dataset
uspto-grants-2009_08
Patent number
US07572816B2

Reaction notes

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