Celestolide → HCID 68161670, compound

HRID 1042061Notes

Reaction equation

HRID 1042061 reaction equation
[CH3:1][C:2]([C:4]1[C:5]2[CH2:6][CH2:7][C:8]([CH3:18])([CH3:17])[C:9]=2[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)=O.[C:19](O)(=O)C.[CH:23]([NH2:25])=[NH:24]>C(O)CCC>[CH3:14][C:13]([C:11]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:18])[CH3:17])=[C:4]([C:2]2[CH:1]=[CH:19][N:25]=[CH:23][N:24]=2)[CH:12]=1)([CH3:16])[CH3:15]

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 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone (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-(1,1-dimethylethyl)-2,3-dihydro-1,1-dimethyl-1H-inden-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-87dfa90d5b5647da8615adf1062477f6
Source dataset
uspto-grants-2013_10
Patent number
US08557827B2

Reaction notes

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