Diethyl Ether → HCID 66765166, compound

HRID 402776Notes

Reaction equation

HRID 402776 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:16](OCC)=[O:17])[CH:5]=1)[CH3:2].CCOCC.CC(C[AlH]CC(C)C)C>CCOC(C)=O>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([CH2:16][OH:17])[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydrideHCID 66765522HCID 66765522, compound

Product 1

HCID 66765166HCID 66765166, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a nitrogen flushed 100 mL round bottom flask were added ethyl 4-ethoxy-8-methoxynaphthalene-2-carboxylate (0.19 g, 0.69 mmol) and dry ether (10 mL). DIBAL (1.7 mL, 1 M in toluene) was added. The reaction mixture was stirred at room temperature for 5 minutes and was then diluted with EtOAc (20 mL). Wet silica gel (10 g silica gel/0.5 mL water) was added. The resulting mixture was stirred for 10 minutes and then filtered and the filtrate was concentrated. The crude product was purified on a silica gel column eluting with a gradient of 100% hexanes to 40% EtOAc/hexanes to give the title intermediate (136 mg) as a white solid.

Workup

  1. customTo a nitrogen flushed 100 mL round bottom flask
  2. additionWet silica gel (10 g silica gel/0.5 mL water) was added
  3. stirringThe resulting mixture was stirred for 10 minutes
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified on a silica gel column
  7. washeluting with a gradient of 100% hexanes to 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-783730cb7a6b480298820c389cc24519
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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