Ammonium Chloride → HCID 19047456, compound

HRID 865966Notes

Reaction equation

HRID 865966 reaction equation
C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][O:9][CH:8]=1.[O:12]1[C:16]2[C:17](=[O:21])[CH2:18][CH2:19][CH2:20][C:15]=2[CH:14]=[CH:13]1.[Cl-].[NH4+]>CCCCCC.CCOCC.C1COCC1>[O:9]1[CH:10]=[CH:11][C:7]([C:17]2([OH:21])[C:16]3[O:12][CH:13]=[CH:14][C:15]=3[CH2:20][CH2:19][CH2:18]2)=[CH:8]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 891643-BromofuranHCID 113209597(4H)-Benzofuranone, 5,6-dihydro-HCID 178418339Butyllithium

Product 1

HCID 19047456HCID 19047456, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 10.2 ml (0.102 mol) of 10M n-butyllithium in hexane in 200 ml of ether cooled to -78° C. was added dropwise 15 g (0.102 mol) of 3-bromofuran and the mixture was stirred for 15 min. To the above cooled mixture was added 12.61 g (0.092 mol) of 4,5,6,7-tetrahydrobenzofuran-7-one in 50 ml of THF and the mixture was allowed to warm to room temperature, and then stirred for 15 min. To the mixture was added saturated ammonium chloride solution and the resulting mixture was extracted with ethyl acetate (3×100 ml), and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford 16.3 g (86%) of 4,5,6,7-tetrahydro-7-(3-furyl)-benzofuran-7-ol, a red oil.

Workup

  1. stirringstirred for 15 min
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×100 ml)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3376f4ddc9154ce99e65c9124f585a2c
Source dataset
uspto-grants-1996_10
Patent number
US05569655

Reaction notes

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