Tert-butyl acetoacetate → HCID 18371104, compound

HRID 1976759Notes

Reaction equation

HRID 1976759 reaction equation
[CH3:1][O:2][CH:3]([CH:6]=[CH2:7])[CH2:4][OH:5].[C:8](OC(C)(C)C)(=[O:13])[CH2:9][C:10]([CH3:12])=[O:11]>>[C:8]([O:5][CH2:4][CH:3]([O:2][CH3:1])[CH:6]=[CH2:7])(=[O:13])[CH2:9][C:10]([CH3:12])=[O:11]

Participants

3

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 27350782-METHOXY-3-BUTEN-1-OL

Product 1

HCID 18371104HCID 18371104, compound

Conditions

Temperature
134 °C

Procedure

In a 500 mL 3-neck round bottom flask was placed 2-methoxy-3-butene-1-ol (164.46 g, 1.61 mol) and t-butyl acetoacetate (430.20 g, 2.50 mol). Reaction flask was equipped with magnetic stir bar, thermocouple, vigreaux column, and a still head with thermometer. Reaction was heated to 134° C. with stirring for 7 hours, then cooled to room temperature. Product was purified using a short-path distillation apparatus. Distillate was collected until the head temperature exceeded 67° C. NMR of the remaining material indicated the desired product. 1H NMR (CDCl3): d 5.63-5.75 (m, 1H), 5.32-5.40 (m, 2H), 5.06 (s, 1H), 4.10-4.25 (m, 2H), 3.82-3.90 (m, 1H), 3.5 (s, 1H), 3.34 (s, 3H), 2.28 (s, 3H), 1.96 (s, 3H).

Workup

  1. customIn a 500 mL 3-neck round bottom flask was placed
  2. customReaction flask
  3. customwas equipped with magnetic stir bar
  4. customReaction
  5. temperaturecooled to room temperature
  6. customProduct was purified
  7. distillationDistillate was collected until the head temperature
  8. customexceeded 67° C

Sources & evidence

ORD record
ord-d29b7dce678d47189cbda52ae03111e0
Source dataset
uspto-grants-2001_05
Patent number
US06228949B1

Reaction notes

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