Imidazole → HCID 18618529, compound

HRID 382839Notes

Reaction equation

HRID 382839 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C@@H:8]2[CH2:12][CH2:11][CH:10]([OH:13])[O:9]2)=[CH:4][CH:3]=1.N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH:8]2[CH2:12][CH2:11][CH:10]([O:13][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10822410(2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran

Product 1

HCID 18618529HCID 18618529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.47 g of (2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran 7 in 30 mL of CH2Cl2 was taken in an100 mL round bottom flask equipped with a magnetic stir bar and nitrogen inlet. That solution was cooled in an ice-water bath and 2.18 g (0.032 mol) of imidazole was added, followed by a solution of 3.6 g (0.024 mol) of tert-butyldimethylsilylchloride (TBDMSCl) in 30 mL of CH2Cl2. The reaction mixture then was stirred at room temperature for 3 hours, and the reaction then quenched with ice water, the organic layer separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography using light petroleum ether:ethyl acetate (9:1) to yield (2S) (4-fluorophenoxymethyl)-5-(tert-butyldimethylsiloxy)-tetrahydrofuran) 8 as an oil (5.1 g, 95%). 1HNMR (200 MHz, CDCl3): γ 0.09 (s, 6 H), 0.88 (s, 9 H), 1.72-2.34 (m, 4 H), 3.76=4.08 (m, 2 H), 4.28-4.54 (m, 1 H), 5.47 (s, 1/3 H), 5.54 (d, J=4.5 Hz, 2/3 H), 6.75-7.0 (m, 4H).

Workup

  1. customequipped with a magnetic stir bar and nitrogen inlet
  2. temperatureThat solution was cooled in an ice-water bath
  3. customthe reaction
  4. customthen quenched with ice water
  5. customthe organic layer separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-12df475a3239413f9ee9025361ad8775
Source dataset
uspto-grants-2001_10
Patent number
US06310221B1

Reaction notes

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