Tetrahydrofuran → HCID 86707588, compound

HRID 2279977Notes

Reaction equation

HRID 2279977 reaction equation
C([O:8][CH2:9][CH2:10][C:11]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[C:22]([C:33]3[CH:38]=[CH:37][C:36]([O:39][C:40](=[O:51])[CH2:41][CH2:42][O:43]CC4C=CC=CC=4)=[CH:35][CH:34]=3)[CH:23]=[C:24]([O:26]COCCOC)[CH:25]=2)=[CH:16][CH:15]=1)=[O:12])C1C=CC=CC=1.C1COCC1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(O)(C)C.CCOCC>[OH:26][C:24]1[CH:25]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][C:11](=[O:12])[CH2:10][CH2:9][OH:8])=[CH:15][CH:16]=2)[CH:21]=[C:22]([C:33]2[CH:34]=[CH:35][C:36]([O:39][C:40](=[O:51])[CH2:41][CH2:42][OH:43])=[CH:37][CH:38]=2)[CH:23]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86707589HCID 86707589, compound

Product 1

HCID 86707588HCID 86707588, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

5.40 g (7.82 mmol) 3-benzyloxy-propionic acid-4″-(3-benzyloxy-propionyloxy)-5′-(2-methoxy-ethoxymethoxy)-[1,1′;3′,1″]terphenyl-4-yl ester are dissolved in 40 ml isopropanol and 10 ml THF and after addition of 1.97 g (7.82 mmol) pyridiniumtosylate are stirred for 60 h at 70° C. After cooling to RT the mixture is diluted with MTB ether, washed with sat. aq. sodium chloride solution and dried over sodium sulfate. The solvent is removed in vacuo and the residue is hydrogenated in 40 ml THF on Pd/activated charcoal until the reaction is completed. The solvent is removed in vacuo and the crude product is recrystallized from dichloromethane, to give 3-hydroxy-propionic acid-5′-hydroxy-4″-(3-hydroxy-propionyloxy)-[1,1′;3′,1″]terphenyl-4-yl ester as colourless crystals.

Workup

  1. temperatureAfter cooling to RT the mixture
  2. washwashed with sat. aq. sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed in vacuo
  5. customThe solvent is removed in vacuo
  6. customthe crude product is recrystallized from dichloromethane

Sources & evidence

ORD record
ord-987733ee9f37406fba736152d460dbee
Source dataset
uspto-grants-2015_09
Patent number
US09133395B2

Reaction notes

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