Imidazole → (R)-1,1,1-trifluoro-4-iodo-2-butanol

HRID 1243612Notes

Reaction equation

HRID 1243612 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[F:27][C:28]([F:35])([F:34])[C@H:29]([OH:33])[CH2:30][CH2:31]O>ClCCl>[F:27][C:28]([F:35])([F:34])[C@H:29]([OH:33])[CH2:30][CH2:31][I:25]

Participants

6

Procedure

Triphenylphosphine (5.09 g, 19.4 mmol) was dissolved in dichloromethane (66 mL) and treated with imidazole (1.33 g, 19.5 mmol) and iodine (4.92 g, 19.4 mmol), respectively, to give an orange suspension. A solution of (R)-4,4,4-trifluoro-1,3-butanediol (2.34 g, 16.2 mmol) in dichloromethane (18 mL) was added to the suspension and stirred for 30 minutes. The reaction mixture was placed on a silica gel flash column and eluted with 100% dichloromethane to give the product as a pale purple oil (3.30 g, 80%).

Workup

  1. customrespectively, to give an orange suspension
  2. washeluted with 100% dichloromethane

Sources & evidence

ORD record
ord-3a3d7e8434af4b97860d89bd8a2ce0ac
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

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