HCID 86700848, compound → HCID 86700849, compound

HRID 881747Notes

Reaction equation

HRID 881747 reaction equation
C([O:3][C:4]([C:6]1([C:19](OCC)=[O:20])[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:8][CH2:7]1)=O)C>O1CCCC1>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH2:10][CH2:11][C:6]([CH2:4][OH:3])([CH2:19][OH:20])[CH2:7][CH:8]=2)=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 86700848HCID 86700848, compound

Product 1

HCID 86700849HCID 86700849, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried flask under nitrogen was charged with 4-(4-chloro-phenyl)-cyclohex-3-ene-1,1-dicarboxylic acid diethyl ester (6.5 g, 19.30 mmol) in tetrahydrofuran (80 ml), and at −78° C. was added lithium alumina hydride (30.9 ml, 30.9 mmol) in one portion. The mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction was quenched with saturated aqueous sodium chloride solution (5 ml) at 0° C. The mixture was filtered and the filtrate was extracted with ethyl acetate (3×100 ml), and the residue solid was washed with acetone (100 ml). The organic solvents were combined, dried over Na2SO4, and concentrated. The residue was purified by chromatography (heptanes/acetone 1/2) to afford [4-(4-chloro-phenyl)-1-hydroxymethyl-cyclohex-3-enyl]-methanol (4.7 g, 96%) as white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.64-1.74 (m, 2H) 2.04 (d, J=3.66 Hz, 2H) 2.37-2.46 (m, 2H) 3.50 (td, J=10.80, 8.80 Hz, 4H) 6.03-6.11 (m, 1H) 7.27 (d, J=8.40 Hz, 2H) 7.36 (d, J=8.40 Hz, 2H).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium chloride solution (5 ml) at 0° C
  2. filtrationThe mixture was filtered
  3. extractionthe filtrate was extracted with ethyl acetate (3×100 ml)
  4. washthe residue solid was washed with acetone (100 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (heptanes/acetone 1/2)

Sources & evidence

ORD record
ord-75ed238992324bb5975ce46865132cc6
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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