Diisobutylaluminum hydride → {5-[2-(Benzyloxy)ethyl]cyclohex-1-en-1-yl}methanol

HRID 133166Notes

Reaction equation

HRID 133166 reaction equation
C[O:2][C:3]([C:5]1[CH2:10][CH:9]([CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][CH2:7][CH:6]=1)=O.CC(C[AlH]CC(C)C)C>C1COCC1>[CH2:14]([O:13][CH2:12][CH2:11][CH:9]1[CH2:10][C:5]([CH2:3][OH:2])=[CH:6][CH2:7][CH2:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 235495385-(2-Benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester

Product 1

HCID 21879600{5-[2-(Benzyloxy)ethyl]cyclohex-1-en-1-yl}methanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Intermediate A3 (6.5 g) was dissolved in THF (100 mL) and added to a solution of DIBAL (70 mL, 1M in hexanes) (available from Aldrich) in THF (160 mL) at −35° C. for 35 m. The mixture was quenched with Rochelle's salt solution, and extracted with ether. The dried residue was purified by chromatography on SiO2 with 30% EtOAc:Hx to yield [5-(2-benzyloxy-ethyl)-cyclohex-1-enyl]-methanol 4.6 g (80%). A solution of the alcohol (4.0 g, 18.7 mmol) in DMF (60 mL) was treated with triethylamine (3 mL) followed by TBSCl (3.0 g, 22.4 mol) for 20 m at rt. The residue was isolated from an aqueous work-up and purified by chromatography to give [5-(2-benzyloxy-ethyl)-cyclohex-1-enylmethoxy]-tert-butyl-dimethyl-silane (Intermediate A4) 3.6 g (63%).

Workup

  1. customThe mixture was quenched with Rochelle's salt solution
  2. extractionextracted with ether
  3. customThe dried residue was purified by chromatography on SiO2 with 30% EtOAc

Sources & evidence

ORD record
ord-b14c494d1ce4419b9047b45bad411310
Source dataset
uspto-grants-2008_06
Patent number
US07390829B2

Reaction notes

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