Lithium → (2,6-Diethoxy-4'-fluorobiphenyl-4-yl)methanol

HRID 409993Notes

Reaction equation

HRID 409993 reaction equation
[Li].[CH2:2]([O:4][C:5]1[CH:10]=[C:9]([C:11](OCC)=[O:12])[CH:8]=[C:7]([O:16][CH2:17][CH3:18])[C:6]=1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH3:3]>C1COCC1>[CH2:2]([O:4][C:5]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]([O:16][CH2:17][CH3:18])[C:6]=1[C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[CH3:3]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 66644576Ethyl 2,6-diethoxy-4'-fluorobiphenyl-4-carboxylate

Product 1

HCID 58408103(2,6-Diethoxy-4'-fluorobiphenyl-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminumhydride (34 ml, 34 mmol) in THF was added dropwise over 30 min to a stirred solution of Compound 2 (14 g, 42 mmol) in THF (120 mL) at room temperature. After 2 h, TLC showed no starting material left. The reaction mixture was stored in the fridge overnight and was quenched by the sequential addition of water (4 mL), aq NaOH (0.5 M, 4 mL) and water (4 mL). The mixture was filtered through CELITE (diatomaceous earth), washed thoroughly with EtOAc and the filtrate was concentrated to give Compound 3 as white solid. H NMR (500 MHz, CDCl3, ppm): 1.3 (t, 6H), 1.8 (t, 1H), 4.0 (q, 4H), 4.7 (d, 2H), 6.7 (s, 2H), 7.1 (m, 2H), 7.4 (m, 2H).

Workup

  1. waitleft
  2. customwas stored in the fridge overnight
  3. customwas quenched by the sequential addition of water (4 mL), aq NaOH (0.5 M, 4 mL) and water (4 mL)
  4. filtrationThe mixture was filtered through CELITE (diatomaceous earth)
  5. washwashed thoroughly with EtOAc
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0b90af14f4a149dc83c08e7092bbad5f
Source dataset
uspto-grants-2014_06
Patent number
US08759539B2

Reaction notes

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