Sodium hydride → HCID 86602758, compound

HRID 349714Notes

Reaction equation

HRID 349714 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH2:5][OH:6])[CH2:3][OH:4].[H-].[Na+].[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:20]Br>CN(C=O)C>[F:15][C:16]([F:29])([F:30])[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:24]=1)[CH2:20][O:4][CH2:3][C:2]([CH3:1])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 906032-Methyl-2-phenylpropane-1,3-diolHCID 1225733,5-Bis(trifluoromethyl)benzyl bromide

Product 1

HCID 86602758HCID 86602758, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Methyl-2-phenylpropane-1,3-diol (3.37 g, 20.3 mmol) was dissolved in DMF, NaH (812 mg, 60%, 20.3 mmol) was added and the mixture was stirred at room temperature for 30 minutes. A DMF solution of 3,5-bistrifluoromethylbenzyl bromide (6.23 g, 20.3 mmol) was added in one portion and stirred for another 1 hour before it was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine and dried with Na2SO4 before being concentrated. The crude product was purified by silica flash chromatography using 15% ethyl acetate in hexanes to yield 4.2 grams (52.8%) of the desired mono-alkylated product. 1H NMR (500 MHz, CDCl3) δ: 1.40 (s, 3 H) 1.78 (s, 1 H) 3.72 (d, J=9.16 Hz, 1 H) 3.82 (d, J=9.16 Hz, 1 H) 3.89 (m, 2 H) 4.64 (s, 2 H) 7.26 (m, 1 H) 7.37 (m, 4 H) 7.72 (s, 2 H) 7.79 (s, 1 H).

Workup

  1. stirringstirred for another 1 hour before it
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationbefore being concentrated
  7. customThe crude product was purified by silica flash chromatography
  8. customto yield 4.2 grams (52.8%) of the desired mono-alkylated product

Sources & evidence

ORD record
ord-a22a66ea4b2a47398f5702d447b8fb8e
Source dataset
uspto-grants-2007_02
Patent number
US07179926B2

Reaction notes

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