4-[3-[1,3]-Dioxolan-2-yl-propyl)benzoic acid methyl ester → [4-(3-[1,3]-Dioxan-2-yl-propyl)phenyl]methanol

HRID 53568

반응식

HRID 53568 반응식
CO[C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[CH:6][CH:5]=1.[H-].[CH2:20]([Al+]CC(C)C)C(C)C>C1COCC1>[O:17]1[CH2:16][CH2:15][CH2:20][O:14][CH:13]1[CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:18])=[CH:9][CH:8]=1

참가 물질

4

반응물 2

HCID 109339244-[3-[1,3]-Dioxolan-2-yl-propyl)benzoic acid methyl esterHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 19694137[4-(3-[1,3]-Dioxan-2-yl-propyl)phenyl]methanol수율 95.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2.85 g (11.4 mmol) of ester 169 in 25 mL of THF at 0° C. was added 4.4 mL (24.7 mmol) of diisobutylaluminum hydride and the resulting mixture was allowed to stir at 0° C. for 15 min. The reaction was quenched with saturated potassium sodium tartrate and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated to yield 2.58 g of the crude alcohol 170 as an oil. 1H NMR consistent with the product.

후처리

  1. customThe reaction was quenched with saturated potassium sodium tartrate
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f72675963b0e426a8fea7f002ccdfc8e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620971

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