Water → HCID 59643043, compound

HRID 2251618Notes

Reaction equation

HRID 2251618 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:16][CH3:17])[C:5]([O:14][CH3:15])=[C:6]([CH:8]2[O:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:7]=1.[Li]C(C)(C)C.[C:23]1([CH3:31])[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=1.O>C1COCC1>[O:9]1[CH2:10][CH2:11][CH2:12][O:13][CH:8]1[C:6]1[CH:7]=[C:2]([CH:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:31])=[CH:24][CH:25]=2)[OH:30])[CH:3]=[C:4]([O:16][CH3:17])[C:5]=1[O:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 15054922HCID 15054922, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59643043HCID 59643043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(5-Bromo-2,3-dimethoxy-phenyl)-[1,3]dioxane (2 g, 6.6 mmol) in 13 mL dry THF cooled to −78° C., t-BuLi (1.5M solution in pentane, 2.5 eq.) was added dropwise via a syringe and the resulting dark red suspension was stirred 30 min. at −78° C. p-Tolualdehyde (1.2 g, 10 mmol, 1.5 eq.) was added dropwise to the mixture and the resulting clear solution was stirred 30 min at −78° C., then 30 min at 0° C. H2O (25 mL) was slowly added and the resulting solution was extracted with EtOAc (3×25 mL). The pooled organic fractions were dried over MgSO4 and evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc 3:2) to yield the desired compound as a colorless solid.

Workup

  1. additionwas added dropwise to the mixture
  2. custom30 min
  3. customat 0° C
  4. extractionthe resulting solution was extracted with EtOAc (3×25 mL)
  5. dry with materialThe pooled organic fractions were dried over MgSO4
  6. customevaporated in vacuo
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-d7555b8597f64d5eb35b287985026f7b
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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