1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57443974, compound

HRID 1172856Notes

Reaction equation

HRID 1172856 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH2:15][OH:16])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])C.C1CCN2C(=NCCC2)CC1>CO>[CH3:1][O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH2:15][OH:16])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57443968HCID 57443968, compound

Product 1

HCID 57443974HCID 57443974, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid ethyl ester (9.45 g, 40.0 mmol) and DBU (6.00 mL, 40.1 mmol) in anhydrous MeOH (200 mL) was allowed to stir for 2 d. After concentration, the residue was dissolved in EtOAc (800 mL) and washed with 1N HCl, water, saturated NaHCO3 and brine. The organic layer was dried, filtered and the filtrate was concentrated and dried to give 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid methyl ester as off white solid. 1H NMR (CDCl3, 200 MHz) δ 8.03 (d, J=0.6 Hz, 1H), 7.90-7.80 (m, 2H), 7.39 (dd, J=8.0, 1.4 Hz, 1H), 4.83 (s, 2H), 3.94 (s, 3H), 1.98 (brs, 1H). MS (EI): cal'd 223.0 (MH+), exp 223.1 (MH+).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in EtOAc (800 mL)
  3. washwashed with 1N HCl, water, saturated NaHCO3 and brine
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customdried

Sources & evidence

ORD record
ord-96d299d80711495485aaf45849b741d7
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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