Veratraldehyde → HCID 67087851, compound

HRID 2175721Notes

Reaction equation

HRID 2175721 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:20]=O.CC([O-])(C)C.[K+]>C1COCC1.CC(O)(C)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])/[CH:20]=[CH:1]/[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1

Participants

6

Reactant 3

HCID 8419VeratraldehydeHCID 146167624-Benzoxazolecarboxylic acid, 2-methyl-, methyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 67087851HCID 67087851, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-methylbenzo[d]oxazole-4-carboxylate (0.63 g, 4.12 mmol) and 3,4-dimethoxybenzaldehyde (0.68 g, 4.12 mmol) in THF (25 mL) and t-BuOH (5 mL) was cooled to −50° C. under nitrogen and treated with a solution of t-BuOK in THF (1.0 mol/L, 4.94 mL, 4.94 mmol) at such a rate that the internal reaction temperature did not exceed −46° C. After 2 hours at −50° C., the cooling bath was removed and the mixture was stirred at room temperature for 12 h in the dark. Water was added and the mixture was made slightly acidic by addition of a 1N HCl solution then extracted with DCM. The organic layers were combined, washed with water and brine then dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography using petroleum ether: ethyl acetate 2:1 (v:v) as eluent to give (E)-methyl 2-(3,4-dimethoxystyryl)benzo[d]oxazole-4-carboxylate (0.30 g, 27%). LC-MS (ES-API); rt 9.25 min; m/z calculated for C19H17NO5 [M+H]+ 340.1, found 340.1.

Workup

  1. customdid not exceed −46° C
  2. customthe cooling bath was removed
  3. additionWater was added
  4. additionthe mixture was made slightly acidic by addition of a 1N HCl solution
  5. extractionthen extracted with DCM
  6. washwashed with water and brine
  7. dry with materialthen dried over sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d67bb47df6ad49efbfed2c031566b5f6
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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