Tetrahydrofuran → HCID 57481688, compound

HRID 902847Notes

Reaction equation

HRID 902847 reaction equation
[I:1][C@H:2]1[C@H:8]2[CH2:9][C@H:5]([C:6](=[O:10])[O:7]2)[CH2:4][CH2:3]1.[O:11]1CCCC1>O.Cl>[OH:7][C@H:8]1[C@H:2]([I:1])[CH2:3][CH2:4][C@@H:5]([C:6]([OH:10])=[O:11])[CH2:9]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 1140249819914-92-2

Product 1

HCID 57481688HCID 57481688, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

(1R*,4R*,5R*)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one (2.8 g) was dissolved in a mixed solvent of tetrahydrofuran (27 ml) and water (3 ml), concentrated hydrochloric acid (0.1 ml) was added, and the mixture was heated under reflux for 1 hour. The solvent was distilled off under reduced pressure to obtain (1R*,3R*,4R*)-3-hydroxy-4-iodocyclohexanecarboxylic acid (3.23 g) as a colorless solid.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-671c3d18388b476c9e451e3a1cae4b4c
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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