Triethylamine → HCID 69932245, compound

HRID 1637790Notes

Reaction equation

HRID 1637790 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C@H:6]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:24][CH:23]=3)[C@H:7]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[CH2:8][O:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:43][C:44]([CH3:49])([CH3:48])[C:45](Cl)=[O:46]>O1CCCC1>[CH3:43][C:44]([CH3:49])([CH3:48])[C:45]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C@H:6]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]4[CH2:32][CH2:33][CH2:34][CH2:35]4)=[CH:24][CH:23]=3)[C@H:7]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=3)[CH2:8][O:9]2)=[CH:4][CH:3]=1)=[O:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 69961215HCID 69961215, compound

Product 1

HCID 69932245HCID 69932245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (±)-cis-7-hydroxy-4-(4-(2-pyrrolidinoethoxy)phenyl)-3-(4-(trifluoromethyl)-phenyl)chromane (2.41 g, 4.98 mmol), triethylamine (3.40 ml, 24.4 mmol), 2,2-dimethylpropanoyl chloride (3.0 ml, 24.4 mmol) and tetrahydrofuran (150 ml) was stirred at room temperature for 4 days. The mixture was filtered to remove inorganic solids, the filter plug being washed with a little extra tetrahydrofuran. The solvents were then evaporated to give a colourless amorphous solid, which was recrystallised from 4:1 ethanol/water (20 ml) to give the product as colourless needles.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove inorganic solids
  3. washthe filter plug being washed with a little extra tetrahydrofuran
  4. customThe solvents were then evaporated
  5. customto give a colourless amorphous solid, which
  6. customwas recrystallised from 4:1 ethanol/water (20 ml)

Sources & evidence

ORD record
ord-cf43859c5d0049f1838d339b0f4e4c83
Source dataset
uspto-grants-2000_03
Patent number
US06043269

Reaction notes

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