HCID 18177916, compound → HCID 18177859, compound

HRID 394930Notes

Reaction equation

HRID 394930 reaction equation
[CH3:1][C:2]([C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:20])([CH3:19])[C:9]=2[CH:8]=1)([CH3:6])[C:3](O)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[CH3:6][C:2]([C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:20])([CH3:19])[C:9]=2[CH:8]=1)([CH3:1])[CH2:3][OH:4]

Participants

5

Reactant 2

HCID 18177916HCID 18177916, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18177859HCID 18177859, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.66 g of 2-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-propanoic acid dissolved in 14 ml THF were treated with 24 ml of 1M lithium aluminium hydride solution in ether. The mixture was stirred at room temperature for 18 hours. The mixture was quenched by slowly adding Na2SO4.H2O until no more H2 evolved. The solid was filtered off and the solvent was evaporated, giving a pale yellow oil which was purified by flask chromatography (SiO2, 10% ethyl acetate/hexanes). 1H NMR (CDCl3): 7.29 (d, J=2.2 Hz, 1H), 7.25 (d, J=8.3 Hz, 1H), 7.12 (dd, J=8.3, 2.2 Hz, 1H), 3.55 (br. d, J=5.4 Hz, 2H), 1.67 (s, 4H), 1.31 (s, 6H), 1.28 (s, 6H), 1.27 (s, 6H).

Workup

  1. customThe mixture was quenched by slowly adding Na2SO4.H2O until no more H2
  2. filtrationThe solid was filtered off
  3. customthe solvent was evaporated
  4. customgiving a pale yellow oil which
  5. customwas purified by flask chromatography (SiO2, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ad981cad57bf468eb7628b7f6382ba7d
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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