tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate → t-Butyl [4-(2-ethoxyethoxy)phenethyl]carbamate

HRID 1197934Notes

Reaction equation

HRID 1197934 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.CS(O[CH2:23][CH2:24][O:25][CH2:26][CH3:27])(=O)=O>CN(C)C=O>[CH2:24]([O:25][CH2:26][CH2:27][O:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[CH:4][CH:3]=1)[CH3:23]

Participants

4

Reactant 2

HCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamateHCID 15067105HCID 15067105, compound

Product 1

HCID 54133570t-Butyl [4-(2-ethoxyethoxy)phenethyl]carbamateYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.06 g of a 55% sodium hydride dispersion in oil were washed with hexane and covered with 85 ml of dimethylformamide. 17.0 g (71.6 mmol) of t-butyl [4-hydroxyphenethyl]carbamate [see F. Rocchiccioli et al., Tetrahedron, 34, 2917 (1978)] were then added while cooling with ice and the reaction mixture was stirred at room temperature for 15 minutes. After cooling to 0° a solution of 12.04 g (71.6 mmol) of 2-ethoxyethyl methanesulfonate in 85 ml of dimethylformamide was added dropwise within 10 minutes and the reaction mixture was subsequently stirred at room temperature for 24 hours. Thereafter, the reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride extracts were dried over magnesium sulfate and evaporated under reduced pressure. The residue obtained was chromatographed on 240 g of silica gel with a mixture of hexane and ethyl acetate as the eluting agent and subsequently recrystallized from ether/hexane, whereby there were obtained 19.1 g of t-butyl [ 4-(2-ethoxyethoxy)phenethyl]carbamate, melting point 56°-57°.

Workup

  1. wash3.06 g of a 55% sodium hydride dispersion in oil were washed with hexane
  2. temperaturewhile cooling with ice
  3. additionwas added dropwise within 10 minutes
  4. stirringthe reaction mixture was subsequently stirred at room temperature for 24 hours
  5. extractionextracted with methylene chloride
  6. dry with materialThe methylene chloride extracts were dried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue obtained
  9. customwas chromatographed on 240 g of silica gel with a mixture of hexane and ethyl acetate as the eluting agent
  10. customsubsequently recrystallized from ether/hexane

Sources & evidence

ORD record
ord-0cee6ff44955464e879c5d89bb2bf16a
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

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