Hydrochloric Acid → HCID 18182548, compound

HRID 1359590Notes

Reaction equation

HRID 1359590 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH2:9][CH:8]([CH2:11][C:12]([O:14]C)=[O:13])[C:7]=2[CH:16]=1)#[N:2].[OH-].[Na+].Cl>C1COCC1.CO.C(OCC)(=O)C>[C:12]([CH2:11][CH:8]1[C:7]2[CH:16]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:10][CH2:9]1)([OH:14])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86586629HCID 86586629, compound

Product 1

HCID 18182548HCID 18182548, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl [5-cyano-2,3-dihydro-benzofuran-3-yl]-acetate (3.73 g, 17.2 mmol) (reference example 10a) in THF:MeOH (2:1, 60 mL) was added aqueous NaOH (16 mL, 2M). The resulting mixture was stirred for 10 min then acidified to pH 1 with 2M aqueous HCl. This mixture was diluted with ethyl acetate and washed, sequentially, with water and brine, dried over MgSO4 and concentrated. The crude solid product was used without further purification. 1H NMR (CDCO3) d 2.70 (dd, 16, 8 Hz, 1H), 2.85 (dd, J=16, 5 Hz, 1H), 3.91 (m, 1H), 4.38 (dd, J=8, 6 Hz, 1H), 4.85 (t, J=8 Hz, 1H), 6.84 (d, J=8 Hz, 1H), 7.47 (m, 2H). MS (EI) m/z 203 (M)+.

Workup

  1. washwashed
  2. dry with materialsequentially, with water and brine, dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude solid product was used without further purification

Sources & evidence

ORD record
ord-a2e17a34bfba48829731fa506600c16e
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

Loading…