Water → [4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-methanol

HRID 556151Notes

Reaction equation

HRID 556151 reaction equation
C([O:3][C:4]([CH:6]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[Cl:23][C:18]1[CH:17]=[C:16]([CH:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][CH:6]([CH2:4][OH:3])[CH2:15]2)[CH:21]=[CH:20][C:19]=1[Cl:22]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 248577544-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester

Product 1

HCID 66808981[4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-methanolYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10 (2.55 g, 7.3 mmol) in THF (40 ml) was added dropwise to a stirring mixture of LiAlH4 (0.304 g, 8.0 mmol) in THF (20 ml) at 0° C. The resulting suspension was stirred at room temperature for 3 hours, then, the mixture was cooled to 0° C., and water (0.15 ml) was added dropwise to destroy the excess hydride. The mixture was filtered, and the solvent was evaporated in vacuo to give colorless oil. The residue was purified by chromatography, CombiFlash silica gel column, MeOH/CH2Cl2, MeOH from 0% to 3%, to give 11 as a clear oil (mixture of cis and trans diastereomers, 1.80 g, 80%). 1H NMR (CDCl3) δ 1.31-1.54 (m, 1H), 1.92-1.98 (m, 2H), 2.10-2.26 (m, 1H), 2.54-2.71 (m, 1H), 2.92-3.03 (m, 1H), 3.53-3.75 (m, 2H), 4.07 (dd, J=12 Hz, 5.2 Hz) and 4.25 (t, J=3.6 Hz, total 1 H), 6.72-7.38 (m, 7H). 13C NMR (CDCl3) δ 32.0, 32.5, 33.4, 34.6, 37.5, 37.6, 43.3, 46.3, 67.5, 67.9, 126.3, 126.4, 126.6, 127.0, 128.4, 128.5, 129.5, 129.7, 130.2, 130.5, 130.7, 130.9, 132.4, 132.7, 136.7, 136.9, 138.8, 147.5, 147.9.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. customto destroy the excess hydride
  3. filtrationThe mixture was filtered
  4. customthe solvent was evaporated in vacuo
  5. customto give colorless oil
  6. customThe residue was purified by chromatography, CombiFlash silica gel column, MeOH/CH2Cl2, MeOH from 0% to 3%

Sources & evidence

ORD record
ord-e1371cc8a226434dadcd93399fbdaea6
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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