N,N-Diethylethanamine trihydrofluoride → HCID 89524950, compound

HRID 1466158Notes

Reaction equation

HRID 1466158 reaction equation
[OH:1][CH2:2][CH:3]1[O:5][CH:4]1[C:6]1[CH:15]=[CH:14][C:9]2[C:10](=[O:13])[O:11][CH2:12][C:8]=2[CH:7]=1.[FH:16].F.F.C(N(CC)CC)C>>[F:16][CH:4]([C:6]1[CH:15]=[CH:14][C:9]2[C:10](=[O:13])[O:11][CH2:12][C:8]=2[CH:7]=1)[CH:3]([OH:5])[CH2:2][OH:1]

Participants

3

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 117599307HCID 117599307, compound

Product 1

HCID 89524950HCID 89524950, compound

Procedure

A solution of 5-[3-(Hydroxymethyl)oxiran-2-yl]-2-benzofuran-1(3H)-one (1.2 g, 5.8 mmol) in TEA.3HF (triethylamine trihydrofluoride) (10 mL) was warmed to 110° C. for 8 hours, and then cooled to RT. The reaction mixture was extracted with EtOAc (200 mL), washed with NaHCO3 (30 mL) and brine (30 mL). The organic layer was dried over Na2SO4, and then concentrated in vacuo. The residue was separated and purified with prep-TLC to give product the title product.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (200 mL)
  2. washwashed with NaHCO3 (30 mL) and brine (30 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was separated
  6. custompurified with prep-TLC

Sources & evidence

ORD record
ord-fbd8499996fb4d9ebda144e6e846451b
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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