Trifluoroacetic acid → HCID 86751988, compound

HRID 727552Notes

Reaction equation

HRID 727552 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][CH:9]([CH3:41])[CH2:10][C:11]1([C:38]([CH3:40])=[CH2:39])[CH2:16][CH:15]([CH2:17][O:18]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:14][C:12]1=[O:13]>C(Cl)Cl>[CH3:8][CH:9]([CH3:41])[CH2:10][C:11]1([C:38]([CH3:40])=[CH2:39])[CH2:16][CH:15]([CH2:17][OH:18])[O:14][C:12]1=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 77754145HCID 77754145, compound

Product 1

HCID 86751988HCID 86751988, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TFA (15.0 mL) is added to a solution of [S-(R*,R*)]-α-(2-methylpropyl)-α-(propen-2-yl)-γ-trityloxymethyl-γ-butyrolactone (2.09 g, 4.60 mmol) and CH2Cl2 (30.0 mL) at 0° C. The solution is stirred for 75 minutes at 0° C. and is concentrated. Aqueous workup (CH2Cl2, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc) provides 684 mg (70%) of the title compound as an oil.

Workup

  1. concentrationis concentrated
  2. customAqueous workup (CH2Cl2, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-bc2282e1a51f4982846e33a257be5e77
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

Loading…