Tetrahydrofuran → HCID 14496321, compound

HRID 704160Notes

Reaction equation

HRID 704160 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH:21]([OH:23])[CH3:22])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 14512984HCID 14512984, compound

Product 1

HCID 14496321HCID 14496321, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

120.9 g (0.4 mol) of 4-benzyloxy-4'-acetylbiphenyl, 400 ml of tetrahydrofuran and 100 ml of methanol were supplied into a four-necked flask provided with a stirrer and a thermometer. Then 15.14 g (0.4 mol) of sodium borohydride 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 twice with 500 ml of chloroform. The organic layer was concentrated under reduced pressure to obtain 117.4 g (96.5% yield) or 4-benzyloxy-4'-(1-hydroxyethyl)-biphenyl (VI-12).

Workup

  1. customprovided with a stirrer
  2. extractionextracted twice with 500 ml of chloroform
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6fd79f4b2f2e43f0850e9d4cc6bdc4ee
Source dataset
uspto-grants-1991_01
Patent number
US04985590

Reaction notes

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