Water → HCID 69831201, compound

HRID 2084360Notes

Reaction equation

HRID 2084360 reaction equation
C([Li])CCC.[C:6]([N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:30]([O:37][CH2:38][C@H:39]1[CH2:41][O:40]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>C1COCC1>[CH2:30]([O:37][CH2:38][C@H:39]([OH:40])[CH2:41][C:26]1[N:25]([C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:29]=[CH:28][N:27]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 159746(-)-Benzyl (R)-glycidyl etherHCID 618231DechloroclotrimazoleHCID 178418339Butyllithium

Product 1

HCID 69831201HCID 69831201, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an argon atmosphere, n-butyllithium (1.6 M solution in hexane, 6.9 ml) was added drop by drop to a solution of 1-tritylimidazole (3.10 g) in THF (80 ml) under ice cooling. After stirring at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52 ml) was added. After stirring under ice cooling for 1.5 hours and at room temperature for 1 hour, water was added and the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saline and dried over magnesium sulfate, after which it was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane 1:1) to yield the titled compound (1.402 g) as a pale-yellow oily substance.

Workup

  1. stirringAfter stirring under ice cooling for 1.5 hours and at room temperature for 1 hour
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationafter which it was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane 1:1)

Sources & evidence

ORD record
ord-4a7c1561ae69474ca23811253acd61c7
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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