4-Aminophenol → HCID 19612300, compound

HRID 1602704Notes

Reaction equation

HRID 1602704 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3([CH3:26])[C:18]4[CH:19]=[C:20]([C:23](O)=[O:24])[CH:21]=[CH:22][C:17]=4[O:16][CH2:15]3)[CH:5]=[CH:4][C:3]1=2.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:53][C:54]1[CH:59]=[CH:58][C:57]([OH:60])=[CH:56][CH:55]=1>C1COCC1.CN(C=O)C.C(OCC)(=O)C.O>[OH:60][C:57]1[CH:58]=[CH:59][C:54]([NH:53][C:23]([C:20]2[CH:21]=[CH:22][C:17]3[O:16][CH2:15][C:14]([C:6]4[CH:5]=[CH:4][C:3]5[C:2]([CH3:27])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=5[CH:7]=4)([CH3:26])[C:18]=3[CH:19]=2)=[O:24])=[CH:55][CH:56]=1

Participants

9

Reactant 4

HCID 4034-AminophenolHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 15840104HCID 15840104, compound

Product 1

HCID 19612300HCID 19612300, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-3-methyl-2H-1-benzofuran-5-carboxylic acid (100 mg, 0.275 mmol), 1-hydroxybenzotriazole (74 mg, 0.55 mmol), 1,3-dicyclohexylcarbodiimide (112 mg, 0.55 mmol) and 4-aminophenol (30 mg, 0.255 mmol) in 5 ml of THF and 2 ml of DMF is stirred at room temperature for 6 hours. 30 ml of water and 30 ml of ethyl acetate are added. After stirring and separation of the phases by settling, the aqueous phase is extracted with 2×30 ml of ethyl acetate. The organic phases are then combined and washed twice with 30 ml of water and then dried over magnesium sulphate, and concentrated on a rotary evaporator under vacuum at 40° C. The product is then purified by flash chromatography on a column of silica (50% heptane/50% ethyl acetate).

Workup

  1. customseparation of the phases
  2. extractionthe aqueous phase is extracted with 2×30 ml of ethyl acetate
  3. washwashed twice with 30 ml of water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  6. customThe product is then purified by flash chromatography on a column of silica (50% heptane/50% ethyl acetate)

Sources & evidence

ORD record
ord-c3f301502854480c9197bbf4df7ee378
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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