(S)-(+)-3-Hydroxytetrahydrofuran → (2-Chloro-5-iodophenyl)(4-(((3S)-tetrahydro-3-furanyl)oxy)phenyl)methanone

HRID 500320Notes

Reaction equation

HRID 500320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=1)=[O:10].[OH:18][C@H:19]1[CH2:23][CH2:22][O:21][CH2:20]1.CC(C)([O-])C.[K+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:18][C@H:19]2[CH2:23][CH2:22][O:21][CH2:20]2)=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 15941366(2-Chlor-5-iod-phenyl)-(4-fluoro-phenyl)-methanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 59423635(2-Chloro-5-iodophenyl)(4-(((3S)-tetrahydro-3-furanyl)oxy)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To a solution of 60.56 g (2-chloro-5-iodo-phenyl)-(4-fluoro-phenyl)-methanone in 170 mL of tetrahydrofuran and 16.46 g of (S)-3-hydroxytetrahydrofuran is added 26 g of potassium tert-butoxide in 250 mL of tetrahydrofuran at 0 to 5° C. The solution is stirred at 10° C. for 0.5 hour. The reaction is quenched with 170 mL of water and 170 mL of methyl tert-butyl ether at 0 to 25° C. The product is washed with 170 mL of brine (3 weight-%). The solvent is removed upon evaporation and crystallized in 220 mL of iso-propylacetate.

Workup

  1. customThe reaction is quenched with 170 mL of water and 170 mL of methyl tert-butyl ether at 0 to 25° C
  2. washThe product is washed with 170 mL of brine (3 weight-%)
  3. customThe solvent is removed upon evaporation
  4. customcrystallized in 220 mL of iso-propylacetate

Sources & evidence

ORD record
ord-0d9d811ccf1541dd93de0e7f4235de3e
Source dataset
uspto-grants-2010_08
Patent number
US07772191B2

Reaction notes

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