Aluminium lithium hydride → HCID 90408594, compound

HRID 1855061Notes

Reaction equation

HRID 1855061 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)([C:8](OCC)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[CH2:1]=[C:2]1[CH2:3][CH2:4][C:5]([CH2:8][OH:9])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90408106HCID 90408106, compound

Product 1

HCID 90408594HCID 90408594, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-methylene-1-(3-phenoxyphenyl)cyclohexanecarboxylate (96 mg, 0.285 mmol) in THF (5 mL) at 0° C. was added lithium aluminum hydride (0.314 mL of a 1.0 M in Et2O; 0.314 mmol). The solution was warmed to rt and stirred for 1 h. The reaction was then quenched at 0° C. by adding EtOAc followed by a saturated aq sodium sulfate. The mixture was diluted with EtOAc and filtered through a pad of CELITE®. The filtrate was dried (Na2SO4) and concentrated in vacuo to afford the title compound (84 mg, 100% yield) as a colorless oil. LCMS, [M+Na]+=317.1. 1H NMR (500 MHz, CDCl3) δ 7.38-7.32 (m, 3H), 7.20-7.16 (m, 1H), 7.15-7.09 (m, 2H), 7.04-7.00 (m, 2H), 6.88 (ddd, J=8.1, 2.3, 0.8 Hz, 1H), 4.63 (s, 2H), 3.53 (s, 2H), 2.28-2.19 (m, 4H), 2.16-2.07 (m, 2H), 1.72-1.64 (m, 2H).

Workup

  1. customThe reaction was then quenched at 0° C.
  2. additionby adding EtOAc
  3. additionThe mixture was diluted with EtOAc
  4. filtrationfiltered through a pad of CELITE®
  5. dry with materialThe filtrate was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5c250a6e1d2473cb528fbdba0271765
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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