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

HRID 53568

反応式

HRID 53568 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f72675963b0e426a8fea7f002ccdfc8e
出典データセット
uspto-grants-1997_04
特許番号
US05620971

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