1-Dodecanol → [1,1':3',1"-Terphenyl]-2'-yl[(dodecyloxy)sulfonyl]carbamate

HRID 5643

반응식

HRID 5643 반응식
Cl[S:2]([NH:5][C:6](=[O:26])[O:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:11]=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:4])=[O:3].[CH2:27]([OH:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C(N(CC)CC)C>C1COCC1>[C:20]1([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]=2[O:7][C:6](=[O:26])[NH:5][S:2]([O:39][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=[O:4])=[O:3])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 81931-DodecanolHCID 8471TriethylamineHCID 10572313[1,1':3',1"-Terphenyl]-2'-yl(chlorosulfonyl)carbamate

생성물 1

HCID 15233160[1,1':3',1"-Terphenyl]-2'-yl[(dodecyloxy)sulfonyl]carbamate수율 42.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of [1,1':3',1"-terphenyl]-2'-yl (chlorosulfonyl)carbamate (5.0 g, 12.9 mmoles) in 75 mL THF was added dropwise to a solution of n-dodecyl alcohol (2.4 g, 12.9 mmoles) and triethylamine (1.3 g, 12.9 mmoles) in 100 mL THF at ~15° C. under an atmosphere of N2. The mixture was allowed to warm to room temperature for 16 hours, then concentrated in vacuo and partitioned between H2O and EtOAc. The EtOAc layer was dried with MgSO4 and evaporated to give a white solid. Chromatography (SiO2, 10% EtOAc/hexanes) gave 2.95 g of the title compound, mp 124°-126° C.

후처리

  1. concentrationconcentrated in vacuo
  2. custompartitioned between H2O and EtOAc
  3. dry with materialThe EtOAc layer was dried with MgSO4
  4. customevaporated
  5. customto give a white solid

출처 및 근거

ORD 기록
ord-77906ee1bea24ed3b1e739a1dc11b691
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245068

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