Sulfuric Acid → 3-(2,3-Dihydrobenzofur-7-yl)-3-methylbutanal

HRID 916046Notes

Reaction equation

HRID 916046 reaction equation
CN(OC)[C:3](=[O:17])[CH2:4][C:5]([C:8]1[C:16]2[O:15][CH2:14][CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6].CC(C[AlH]CC(C)C)C.S(=O)(=O)(O)O.C(OCC)(=O)C>C1COCC1>[O:15]1[C:16]2[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][CH:3]=[O:17])=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 589600233-(2,3-dihydrobenzofur-7-yl)-3-methylbutanoic acid N,O-dimethylhydroxylamide

Product 1

HCID 589599393-(2,3-Dihydrobenzofur-7-yl)-3-methylbutanalYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(2,3-Dihydrobenzofur-7-yl)-3-methylbutanoic acid N,O-dimethylhydroxylamide (950 mg) in THF (10 mL) was treated with DIBAL (1 M in toluene, 4.32 mL) at −78° C. After 45 minutes, the mixture was warmed to 0° C. for 5 minutes. 7 mL of aqueous sulfuric acid (1 M) and 20 mL of ethyl acetate were added. The organic phase was separated and the aqueous layer was extracted with 20 mL of ethyl acetate. The combined organic phases were dried over magnesium sulfate. The solvent was removed to give 720 mg (98%) of 3-(2,3-dihydrobenzofur-7-yl)-3-methylbutanal as a yellow oil.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with 20 mL of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-924eac7c0065485b9832efdddca3a94a
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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