Ethyl Acetate → HCID 19707473, compound

HRID 726920Notes

Reaction equation

HRID 726920 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH2:17][CH2:18][CH2:19][CH3:20].C(OCC)(=[O:23])C.C([O-])(O)=O.[Na+]>C1COCC1.CCCCCC>[OH:23][CH2:17][CH2:18][CH2:19][CH2:20][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 661394-PhenoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 19707473HCID 19707473, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-phenoxybenzaldehyde (704 mg, 3.56 mmol) in 15 mL of THF at -78° C. was added n-BuLi dropwise (3.73 mmol, 2.5M in hexane). After 24 hours, the reaction was poured into ethyl acetate and sat. aq. NaHCO3 solution, then washed with brine, dried (Na2SO4) and concentrated in vacuo to provide the crude product.

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b16357306bf43d9bafdbd5422b3dd0e
Source dataset
uspto-grants-1998_01
Patent number
US05710171

Reaction notes

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