Water → HCID 23599741, compound

HRID 891257Notes

Reaction equation

HRID 891257 reaction equation
[OH:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=1O.C(Cl)Cl.[OH2:13]>FC(F)(F)C(O)=O>[OH:13][C@@H:7]1[C@@H:2]([OH:1])[CH2:3][C:4](=[O:8])[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 11083903HCID 11083903, compound

Product 1

HCID 23599741HCID 23599741, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The α,β-unsaturated ketone 9 (FIG. 6) (0.344 g, 1.42 mmol) was stirred in a mixture of trifluroacetic acid (18 mL), CH2Cl2 (2 mL) and water (2 mL) for 30 minutes at 0° C. Solvents were removed in vacuo. The residue was azotroped with toluene (20 ml) and purified by flash chromatography to give compound 2 (FIG. 4) as a white solid (0.137 g, 75%). 1H NMR (D2O) δ 7.04 (dd, J=10.2, 2.4 Hz, 1H), 6.08 (dm, J=10.2 Hz, 1H), 4.45 (dm, J=8.4 Hz, 1H), 3.99-4.07 (m, 1H), 2.82 (ddd, J=16.4, 4.8, 1.2 Hz, 1H), 2.58 (dd, J=16.4, 11.9 Hz, 1H); 13C NMR (D2O) δ 204.8, 156.1, 131.4, 74.4, 74.3, 46.5.

Workup

  1. customSolvents were removed in vacuo
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9f83c2630d4244c38761a61a75f56acb
Source dataset
uspto-grants-2006_02
Patent number
US07002047B2

Reaction notes

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