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

HRID 1197934노트

반응식

HRID 1197934 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-0cee6ff44955464e879c5d89bb2bf16a
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278148

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