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Dimethylformamide → 3,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl-N-[4-(3,5-di-t-butyl-4-hydroxyphenyl)butyl]acrylamide

HRID 1792984
Notes
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Reaction equation

HRID 1792984 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[CH:8]=[C:9]([CH:20]=[CH:21]C(O)=O)[CH:10]=[C:11]([O:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[C:12]=1[OH:13])[CH2:4][CH3:5])[CH3:2].NCCCC[C:30]1[C:31]([C:41]([CH3:44])([CH3:43])[CH3:42])=[C:32]([OH:40])[C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:34][CH:35]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:56]2[CH:57]=[CH:58]C=C[C:55]=2[N:54]=N1.CN([CH:75]=[O:76])C>CCN(CC)CC.C(Cl)Cl>[CH2:18]([CH:15]([O:14][C:11]1[CH:10]=[C:9]([C:20](=[CH2:21])[C:75]([NH:54][CH2:55][CH2:56][CH2:57][CH2:58][C:35]2[CH:30]=[C:31]([C:41]([CH3:42])([CH3:44])[CH3:43])[C:32]([OH:40])=[C:33]([C:36]([CH3:37])([CH3:39])[CH3:38])[CH:34]=2)=[O:76])[CH:8]=[C:7]([O:6][CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[C:12]=1[OH:13])[CH2:16][CH3:17])[CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69639651HCID 69639651, compoundHCID 1298022354-Aminobutyl-2,6-di-t-butylphenol

Product 1

HCID 1317258623,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl-N-[4-(3,5-di-t-butyl-4-hydroxyphenyl)butyl]acrylamide
Yield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 3-[3,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl]acrylic acid (30 mg, 0.09 mmol) in DMF (0.6 ml) and Et3N (13 μl) was added 4-(4-aminobutyl-2,6-di-t-butylphenol (28 mg, 0.10 mmol) at 0° C. and was added the solution of BOP (44 mg, 0.10 mmol) in CH2Cl2 (0.6 ml). The solution was stirred for 30 minutes at 0° C. and then was stirred for 2 hours at room temperature. And then CH2Cl2 was evaporated in vacuo and the obtained residue was poured into ice water. The residue was extracted with EtOAc and washed with HCl (aq) and NaHCO3 (aq). And then the water was dried over anhydrous magnesium sulfate and filtered. The obtained filtrate was vacuum concentrated to give the residue, which was purified by column chromatography (EtOAc:Hexane=1:5), yielding 48 mg (90%) of the title compound as a brown oil.

Workup

  1. stirringwas stirred for 2 hours at room temperature
  2. customAnd then CH2Cl2 was evaporated in vacuo
  3. additionthe obtained residue was poured into ice water
  4. extractionThe residue was extracted with EtOAc
  5. washwashed with HCl (aq) and NaHCO3 (aq)
  6. dry with materialAnd then the water was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the residue, which
  10. customwas purified by column chromatography (EtOAc:Hexane=1:5)

Sources & evidence

ORD record
ord-b8d388da673d433cbe34ec1ef9a357e2
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07078407B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes