tert-Butyl acrylate → HCID 86638179, compound

HRID 1514984Notes

Reaction equation

HRID 1514984 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:13]=[C:12]([CH3:14])[C:9]([CH:10]=[O:11])=[C:8]([CH3:15])[CH:7]=1.[H+].[B-](F)(F)(F)F.[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH:23]=[CH2:24]>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:27]([O:26][C:22](=[O:25])[CH:23]=[CH:24][C:6]1[CH:13]=[C:12]([CH3:14])[C:9]([CH:10]=[O:11])=[C:8]([CH3:15])[CH:7]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 15458tert-Butyl acrylateHCID 28118Tetrafluoroboric acidHCID 123812354-Amino-2,6-dimethylbenzaldehydeHCID 23668193Sodium Nitrite

Product 1

HCID 86638179HCID 86638179, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of NaNO2 (102 mg) in water (1 mL) was added to an ice cold mixture of 4-amino-2,6-dimethylbenzaldehyde (Example 5-1, step 3) (220 mg) and 48% HBF4 (0.5 mL). After 30 min at 0° C., tert-butyl acrylate (0.43 mL) and Pd(OAc)2 (10 mg) were added and the mixture was heated to 80° C. (or in a water bath) for 30 min. The suspension was filtered through Celite, washed with CH2Cl2 and the filtrate extracted with CH2Cl2. The combined organic layers were dried, filtered and concentrated. The residue was purified by flash chromatography using hexanes/ethyl acetate (7:1) and gave 3-(4-formyl-3,5-dimethylphenyl)-acrylic acid tert-butyl ester.

Workup

  1. filtrationThe suspension was filtered through Celite
  2. washwashed with CH2Cl2
  3. extractionthe filtrate extracted with CH2Cl2
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0ec9d0a623364864adb8903d448ac319
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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