Aluminium lithium hydride → 4-(Cycloheptylidene(4-[(2-hydroxy-1,1-dimethylethyl)oxy]phenyl}methyl)phenol

HRID 2100191Notes

Reaction equation

HRID 2100191 reaction equation
[C:1]1(=[C:8]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([CH3:23])([CH3:22])[C:17](OCC)=[O:18])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1(=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([CH3:23])([CH3:22])[CH2:17][OH:18])=[CH:11][CH:10]=2)[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68654317Ethyl 2-({4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}oxy)-2-methylpropanoate

Product 1

HCID 113375544-(Cycloheptylidene(4-[(2-hydroxy-1,1-dimethylethyl)oxy]phenyl}methyl)phenolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reduction procedure described for 224 was used. Ethyl 2-({4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}oxy)-2-methylpropanoate (225) (0.125 g, 0.31 mmol) was treated with LiAlH4 (0.8 mL) in THF (5 mL). Standard work-up followed by purification afforded 0.086 g (76%) of the title compound 230 as white foam. 1H NMR (300 MHz, DMSO-d6): δ 9.27 (s, 1H), 7.00 (d, J=7.8 Hz, 2H), 6.91 (d, J=4.5 Hz, 4H), 6.68 (d, J=8.4 Hz, 2H), 4.84 (t, J=5.7 Hz, 1H), 3.34 (d, J=3.6 Hz, 2H), 2.21 (br s, 4H), 1.52 (br s, 8H), 1.17 (s, 6H). LCMS (ESI): m/z 367 (M−H)−.

Workup

  1. customStandard work-up followed by purification

Sources & evidence

ORD record
ord-34db56dd0c5f4e429ec3873792f82dab
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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