Water → 2-[1,3-Dithian-2-yl]-5-nitrobenzyl alcohol

HRID 280843

반응식

HRID 280843 반응식
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[C:9](O)=[O:10].B.C1COCC1.O>O1CCCC1>[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[CH2:9][OH:10]

참가 물질

5

반응물 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuran2회HCID 135302822-[1,3-Dithian-2-yl]-5-nitrobenzoic acid

생성물 1

HCID 135302832-[1,3-Dithian-2-yl]-5-nitrobenzyl alcohol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice cooled, stirred solution of the Compound 3b (5.00 g, 17.5 mmol) in tetrahydrofuran (100 mL) was added dropwise over 30 minutes 1.0M BH3.THF (20 mL). The solution was allowed to warm to room temperature and was stirred overnight. Additional 1.0M BH3.THF (5 mL) was added, and the solution was stirred another 4 hours. Water was added to hydrolyze the reaction, and the solution then was evaporated to dryness. The residue was dissolved in diethyl ether, and this solution was washed with a saturated solution of sodium carbonate, brine, and was dried over anhydrous magnesium sulfate. Evaporation of the solvent and recrystallization of the product from acetonitrile afforded the Compound 3c; m.p. 130°-131° C.; IR 3600 cm-1 (OH); 1H NMR (CDCl3 +D2O) δ1.8-2.2 (m, 2H, --CH2CH2CH2 --), 2.8-3.2 (m, 4H, --CH2CH2CH2 --), 4.61 (s, 2H, CH2O), 5.48 (s, 1H, SCHS), 7.7-8.3 (m, 3H, ArH).

후처리

  1. stirringthe solution was stirred another 4 hours
  2. customthe reaction
  3. customthe solution then was evaporated to dryness
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washthis solution was washed with a saturated solution of sodium carbonate, brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customEvaporation of the solvent and recrystallization of the product from acetonitrile

출처 및 근거

ORD 기록
ord-3941b52bb5284c31a978a5e6ff1909ba
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04591587

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