Tetrahydrofuran → HCID 14549129, compound

HRID 2051452Notes

Reaction equation

HRID 2051452 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].O1CCCC1.[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 14597215HCID 14597215, compound

Product 1

HCID 14549129HCID 14549129, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33.0 g (0.1 mol) of benzyl 4'-acetyl-4-biphenylcarboxylate, 200 ml of tetrahydrofuran and 50 ml of ethanol were supplied into a four-necked flask provided with a stirrer and a thermometer. Then 3.8 g (0.1 mol) of sodium borohydride was added at 15°-25° C. over a period of 10 minutes. The mixture was maintained at the same temperature for 2 hours. The reaction mixture was poured into ice-water and extracted twice with 300 ml of chloroform. The organic layer was washed with water and concentrated under reduced pressure to obtain 32.9 g (99% yield) of benzyl 4'-(1-hydroxyethyl)-4-biphenylcarboxylate (III-25).

Workup

  1. customprovided with a stirrer
  2. temperatureThe mixture was maintained at the same temperature for 2 hours
  3. extractionextracted twice with 300 ml of chloroform
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e25574959e64af790ccce8a5cd8d720
Source dataset
uspto-grants-1991_05
Patent number
US05019298

Reaction notes

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