Diethyl Ether → HCID 10484675, compound

HRID 1647540Notes

Reaction equation

HRID 1647540 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([C:17]2[C:29]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[CH:19][C:18]=2[O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:16])=[C:13]([C:46]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:47])[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC>N1C2C(=CC=CC=2)C=CC=1>[CH2:1]([O:8][C:9]1[C:14]([C:15]([C:17]2[C:29]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=2[O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:16])=[C:13]([C:46]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:47])[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 10395192HCID 10395192, compound

Product 1

HCID 10484675HCID 10484675, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

A solution of 0.428 g (0.582 mmol) of 1,1-dimethylethyl 4-(6-benzyloxy-2-(benzyloxycarbonyl)benzoyl)-3,5-dibenzyloxybenzoate in 5 mL of distilled quinoline was heated at 200° C. under an atmosphere of nitrogen for 3 h. The mixture was then cooled, poured onto 75 mL of ether and washed three times with 2N HCl and once with brine. The organic extracts were dried over magnesium sulfate and evaporated to give 0.42 g of the crude product, which was recrystallized from isopropanol to give 0.270 g (68%) of the title compound as a tan solid, mp 151°-156° C.

Workup

  1. temperatureThe mixture was then cooled
  2. washwashed three times with 2N HCl
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. customevaporated
  5. customto give 0.42 g of the crude product, which
  6. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-ea6f115c62d84435bf429e7a4ae7028a
Source dataset
uspto-grants-1995_07
Patent number
US05432198

Reaction notes

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