Benzaldehyde → HCID 67744360, compound

HRID 1654712Notes

Reaction equation

HRID 1654712 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[CH:4][C:3]=1[CH3:16].[CH3:17][OH:18].O.C([Li])CCC.C(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.O.CCCCCC>[C:26]1([C:2]2[CH:15]=[CH:14][C:5]([CH:6]([CH2:17][OH:18])[O:7][CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][O:9]3)=[CH:4][C:3]=2[CH3:16])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 22242641Methanol--water (1/1)HCID 22408116HCID 22408116, compoundHCID 178418339Butyllithium

Product 1

HCID 67744360HCID 67744360, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

2-(4-Bromo-3-methylbenzyloxy)tetrahydropyran (1.4 g, 5 millimol) was dissolved in tetrahydrofuran (5 ml), and cooled to -20° C. with methanol-water. Under nitrogen atmosphere, thereto was added 15% hexane solution (5 ml) of n-butyllithium, and in this state, the mixture was stirred for 30 minutes. Next, benzaldehyde (0.6 ml, 6 millimol) was added, and stirred for 2 hours. During this procedure, inner-temperature was raised from -20° C. to 30° C. Then, water was added, and the mixture was extracted with ethyl acetate. After washing with water and saturated aqueous sodium chloride solution, the solvent was distilled away, and the residue was separated and purified by using a silica-gel column chromatography (ethyl acetate:n-hexane=1:5 to 1:2) to give the title compound (0.9 g, 2.9 millimol).

Workup

  1. stirringstirred for 2 hours
  2. temperatureDuring this procedure, inner-temperature was raised from -20° C. to 30° C
  3. extractionthe mixture was extracted with ethyl acetate
  4. washAfter washing with water and saturated aqueous sodium chloride solution
  5. distillationthe solvent was distilled away
  6. customthe residue was separated
  7. custompurified

Sources & evidence

ORD record
ord-ea8b2bc6615e4f56a6cd31bab09ebf78
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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