Diethyl Ether → HCID 15157462, compound

HRID 2371629Notes

Reaction equation

HRID 2371629 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH2:3]1.S(Cl)(Cl)=O.[CH2:44]([O:51][CH2:52][CH:53](O)[CH2:54][O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[CH2:64]([O:66][CH2:67][CH3:68])[CH3:65]>C1C=CC=CC=1.C(Cl)Cl.N1C=CC=CC=1>[C:65]1([CH2:64][O:66][CH2:67][CH:68]([O:33][C:32](=[O:34])[CH2:31][CH2:30][C:4]2([CH2:35][CH2:36][C:37]([O:39][CH:53]([CH2:52][O:51][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH2:54][O:55][CH2:56][C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)=[O:38])[CH2:3][C:2](=[O:1])[C:7]3[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]4[C:29]5[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=5[CH:23]=[CH:22][CH:21]=4)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=3[O:5]2)[CH2:18][O:19][CH2:20][C:29]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 2476141,3-Bis(benzyloxy)propan-2-olHCID 15157460HCID 15157460, compound

Product 1

HCID 15157462HCID 15157462, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 500 mg (0.928 mmol) of the titled product of Example 43 and 0.5 ml of thionyl chloride in 10 ml of benzene was stirred at reflux for 1.5 hours. The mixture was allowed to cool, and the solvent was removed under reduced pressure. The residue was dissolved in 4 ml of methylene chloride (CH2Cl2), a solution of 1.19 g (4.38 mmol) of 1,3-dibenzyloxy-2-propanol in 2 ml of methylene chloride and 2 ml of pyridine was added, and the mixture was stirred at room temperature for three days. To the mixture was added 50 ml of diethyl ether, and the resulting mixture washed successively with dilute hydrochloric acid, with water, and with brine. The solution was dried over magnesium sulfate, the drying agent removed by filtration, and the solvent was removed on a rotary evaporator. Chromatography over a silica gel column using a solvent gradient of 20% increasing to 50% of ethyl acetate/hexane gave 373 mg of the title compound.

Workup

  1. temperatureat reflux for 1.5 hours
  2. temperatureto cool
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in 4 ml of methylene chloride (CH2Cl2)
  5. stirringthe mixture was stirred at room temperature for three days
  6. washthe resulting mixture washed successively with dilute hydrochloric acid, with water
  7. dry with materialThe solution was dried over magnesium sulfate
  8. customthe drying agent removed by filtration
  9. customthe solvent was removed on a rotary evaporator
  10. temperatureincreasing to 50% of ethyl acetate/hexane

Sources & evidence

ORD record
ord-03e5dcf004c043ec8963a1f663b74c55
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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