Triethylamine → HCID 13976416, compound

HRID 2203040Notes

Reaction equation

HRID 2203040 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:16]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17]1>CN(C=O)C>[C:1]([Si:5]([CH3:8])([CH3:7])[O:22][CH2:21][C:18]1[CH:19]=[CH:20][S:16][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 123570Thiophene-3-methanol

Product 1

HCID 13976416HCID 13976416, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyldimethylchlorosilane (1.58 g), triethylamine (2.44 ml), 3-thiophenemethanol (0.822 ml) and DMF (20 ml) was stirred at 60° C. for 1 h. Additional DMF (20 ml) was added to the reaction mixture, and the mixture was stirred at 60° C. for 2 h. The mixture was quenched with saturated NaHCO3 solution, and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane) to give the title compound (1.6 g) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 60° C. for 2 h
  2. customThe mixture was quenched with saturated NaHCO3 solution
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine successively
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-f1023670710240c9b955ea1f0690b99c
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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