Tert-butyl acetoacetate → HCID 18371104, compound

HRID 1700040Notes

Reaction equation

HRID 1700040 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-9827e857cc574a54ad56b14f878dd476
Source dataset
uspto-grants-2002_02
Patent number
US06348623B2

Reaction notes

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