Tetrahydrofuran → HCID 14496321, compound

HRID 704162Notes

Reaction equation

HRID 704162 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].O1CCCC1.B.[Na]>CO>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14512984HCID 14512984, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 14496321HCID 14496321, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12.09 g (0.04 mol) of 4'-acetyl-4-benzyloxybiphenyl (VII-23), 40 ml of tetrahydrofuran and 10 ml of methanol were supplied into a four-necked flask provided with a stirrer and a thermometer. Then 1.51 g (0.4 mol) of sodium boron hydride was added at 15°-25° C. over a period of 2 hours. The mixture was kept at the same temperature for 5 hours, then poured into ice-water and extracted with 50 ml of chloroform. The organic layer was concentrated under reduced pressure to give 11.0 g (95% yield) of 4-benzyloxy-4'-(1-hydroxyethyl)biphenyl (VI-23).

Workup

  1. customprovided with a stirrer
  2. extractionextracted with 50 ml of chloroform
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bca63a586eed4d13bad98483664ffcfe
Source dataset
uspto-grants-1991_01
Patent number
US04985590

Reaction notes

Loading…