Diethyl Ether → HCID 57577374, compound

HRID 1921692Notes

Reaction equation

HRID 1921692 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[C:5]([NH:30][C:31](=[O:33])[CH3:32])([CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=2)[CH:12]1O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(OCC)C>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4](=[O:34])[C:5]([NH:30][C:31](=[O:33])[CH3:32])([C:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=2)[CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 57577369HCID 57577369, compound2×

Product 1

HCID 57577374HCID 57577374, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

2-Acetylamino-2-(6-octyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-malonic acid diethyl ester (compound A, 755 mg, 1.58 mmol)) is dissolved in acetic anhydride (5 mL) followed at 0° C. by a catalytic amount of ferric chloride (66 mg, 0.4 mmol). The reaction is stirred at 0° C. for an additional 2 hours, and 20 mL of diethyl ether is added. The reaction is carefully poured into 50 mL of ice cold water and the organic layer quickly separated. The organic layer is re-extracted with methylene chloride (2×20 mL) and the combined organic layers were washed once with brine (20 mL) and dried over magnesium sulfate. The organic layer is concentrated under vacuum and the residue is purified by column chromatography (silica gel, 10% ethyl acetate in hexanes) to provide 458 mg of compound B (60%). The complete synthesis is illustrated in FIG. 4.

Workup

  1. customthe organic layer quickly separated
  2. extractionThe organic layer is re-extracted with methylene chloride (2×20 mL)
  3. washthe combined organic layers were washed once with brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe organic layer is concentrated under vacuum
  6. customthe residue is purified by column chromatography (silica gel, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4b856796121f4e63ac81eaa51146ff53
Source dataset
uspto-grants-2012_05
Patent number
US08173710B2

Reaction notes

Loading…