Celestolide → HCID 68161670, compound

HRID 1042413Notes

Reaction equation

HRID 1042413 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2([CH3:15])[CH3:14])=[C:7]([C:16](=O)[CH3:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:19](O)(=O)C.[CH:23]([NH2:25])=[NH:24]>C(O)CCC>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2([CH3:15])[CH3:14])=[C:7]([C:16]2[CH:17]=[CH:19][N:25]=[CH:23][N:24]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 61585CelestolideHCID 160693Formamidine acetate

Product 1

HCID 68161670HCID 68161670, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
125 °C

Procedure

A 5 L reaction vessel was charged with 1-(6-tert-butyl-1,1-dimethyl-indan-4-yl)-ethanone (300 g, 1.2 mol) (commercially available at IFF), formamidine acetate (639 g, 6.1 mol), and butanol (1.0 L). The reaction mixture was heated to 125° C. for 10 hours and then cooled to 25° C. The reaction mixture was washed twice with brine (1 L) and purified by vacuum distillation to afford 4-(6-tert-butyl-1,1-dimethyl-indan-4-yl)-pyrimidine (200 g) having a boiling point of 180° C. at a pressure of 0.5 mmHg

Workup

  1. customA 5 L reaction vessel
  2. temperaturecooled to 25° C
  3. washThe reaction mixture was washed twice with brine (1 L)
  4. distillationpurified by vacuum distillation

Sources & evidence

ORD record
ord-eb9c343b0b934b0688334d392832f359
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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