Tetrahydrofuran → 4-[(5-Bromo-4-methylthiophen-2-yl)methyl]morpholine

HRID 606591Notes

Reaction equation

HRID 606591 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=O)=[CH:4][C:3]=1[CH3:15].C1COCC1.[OH-].[Na+]>CO>[Br:1][C:2]1[S:6][C:5]([CH2:7][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:4][C:3]=1[CH3:15]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 67047076(5-Bromo-4-methylthiophen-2-yl)(morpholin-4-yl)methanone

Product 1

HCID 670468844-[(5-Bromo-4-methylthiophen-2-yl)methyl]morpholine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5-Bromo-4-methyl-thiophen-2-yl)-morpholin-4-yl-methanone (1.78 mmol) was added to a flask containing 1M THF.BH3 complex in THF (4.45 mmol). Reaction was stirred at reflux for 2.5 h under N2. Methanol was then added until gas evolution ceased, followed by 10 ml of 1M NaOH and the reaction stirred at reflux for a further 7 h. The mixture was cooled to room temperature and extracted with EtOAc. This extract was concentrated in vacuo and the residue taken up in 1M HCl and washed with EtOAc. The acid layer was then basified with 1M NaOH and extracted back into EtOAc. Removal of solvent gave 4-(5-Bromo-4-methyl-thiophen-2-ylmethyl)-morpholine as a colourless oil: m/z in MS ES+=276, 278 [M+H]+, 0.98 mmol, 55%.

Workup

  1. customReaction
  2. temperatureat reflux for 2.5 h under N2
  3. stirringthe reaction stirred
  4. temperatureat reflux for a further 7 h
  5. extractionextracted with EtOAc
  6. concentrationThis extract was concentrated in vacuo
  7. washwashed with EtOAc
  8. extractionextracted back into EtOAc
  9. customRemoval of solvent

Sources & evidence

ORD record
ord-43218192c2f14ede84b9259aa2e2b89c
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

Loading…