Tert-butyl acetoacetate → HCID 18371104, compound

HRID 1954436Notes

Reaction equation

HRID 1954436 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-36181dd9b91d489f97ca94731acc099d
Source dataset
uspto-grants-2000_09
Patent number
US06121399

Reaction notes

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