Tetrahydrofuran → HCID 54016733, compound

HRID 231013Notes

Reaction equation

HRID 231013 reaction equation
[C:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24](Cl)=[O:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1COCC1.[Cl:32][C@H:33]([CH3:36])[CH2:34][OH:35].C(N(CC)CC)C>CCOCC>[Cl:32][CH:33]([CH3:36])[CH2:34][O:35][C:24]([C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][C:1]([O:3][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:2])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1)=[O:25]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 181530(R)-(-)-2-Chloropropan-1-olHCID 15065826HCID 15065826, compound

Product 1

HCID 54016733HCID 54016733, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

61.5 m moles(22.6 g) of 4'-carbobenzoxyoxybiphenyl-4-carboxylic acid chloride was added dropwise into a THF solution of 61.5 m moles(5.2 g) of (R)-(-)-2-chloro-1-propanol and 10 ml of triethylamine, and stirred for 6 hours. After the reaction, the reaction solution was ether extracted. The extrate was purified by column chromatography to obtain 15.9 g of the ester compound [[α]D23 =+22.5°(CHCl3)]. (yield: 61%)

Workup

  1. customAfter the reaction
  2. extractionextracted
  3. customThe extrate was purified by column chromatography

Sources & evidence

ORD record
ord-0e526531c1e1439f9d259548e0dfb877
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Reaction notes

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