Hydrochloric Acid → HCID 54216858, 화합물

HRID 275178노트

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HRID 275178 반응식
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:8]=[O:9])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][OH:9])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 200905923-Acetoxy-4-pentyloxy-benzaldehyde

생성물 1

HCID 54216858HCID 54216858, 화합물수율 90%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

3-Acetoxy-4-pentyloxy-benzaldehyde (0.75 g., 3.0 mmol, 1 equiv.) is dissolved in 15 mL of MeOH, and the mixture cooled to 0° C. Sodium borohydride (0.230 g., 6 mmol., 2 equiv.) is added in portions. After stirring for 30 min., the mixture is neutralized with 1N HCl, and then extracted thrice with ether. The extracts are washed with brine, dried (MgSO4), and evaporated. Chromatography on silica gel using CH2Cl2 /hexane affords 3-acetoxy-4-pentyloxy-benzyl alcohol (12f) (0.680 g., 2.70 mmol., 90%): mp=35°-36° C.; 1H NMR (300 MHz, CDCl3) δ 7.17 (dd, J=2, 8 Hz, 1H, ArH), 7.05 (d, J=2 Hz, 1H, ArH), 6.92 (d, J=8 Hz, 1H, ArH), 4.85 (s, 1H, OH), 4.60 (s, 2H, ArCH2O), 3.95 (t, J=7 Hz, 2H, OCH2R), 2.30 (s, 3H, CH3CO), 1.75 (m, 2H, OCH2CH2), 1.38 (m, 4H, CH2CH2CH3), 0.90 (t, J=7 Hz, 3H, RCH2CH3).

후처리

  1. extractionextracted thrice with ether
  2. washThe extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-aa3c10a639cf41c387fec4dcf678e762
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391817

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