Triethylamine → HCID 23282096, compound

HRID 2255123Notes

Reaction equation

HRID 2255123 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O-:7])=[O:6].[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[CH2:20](N(CC)CC)C>C(Cl)Cl>[CH3:16][C:15]([Si:12]([CH3:14])([CH3:13])[O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:20])=[O:6])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 178425898HCID 178425898, compound

Product 1

HCID 23282096HCID 23282096, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-hydroxy-4-methylbenzoate (5.55 g, 33 mmol) from Preparation 12, tert-butyldimethylsilyl chloride (7.6 g, 50 mmol), and triethylamine (14 mL, 100 mmol) in 50 mL CH2Cl2 is stirred at room temperature for 24 hours. An additional 25 mL of CH2Cl2 is added and washed with water. The organic layer is dried (MgSO4) and concentrated. The product is isolated by silica gel chromatography (100% CH2Cl2). An oil of methyl 3- [[(1,1-dimethylethyl)-dimethylsilyl]oxy]-4-methylbenzoate is obtained (9.05 g, 97%).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe product is isolated by silica gel chromatography (100% CH2Cl2)

Sources & evidence

ORD record
ord-2f2d9feaa25d43d49008e4324ad77d89
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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