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

HRID 889

Reaction equation

HRID 889 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-e4b7283463484f78b8ff3e4f5af4a115
Source dataset
uspto-grants-1998_03
Patent number
US05723459

Linked notes

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