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

HRID 53568

Reaction equation

HRID 53568 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f72675963b0e426a8fea7f002ccdfc8e
Source dataset
uspto-grants-1997_04
Patent number
US05620971

Linked notes

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