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Diethyl Ether → HCID 14439127, compound

HRID 1849948
Notes
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Reaction equation

HRID 1849948 reaction equation
[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:24]([O-:27])([O-])=O.[Cs+].[Cs+].CCO[CH2:33][CH3:34]>CN(C)C=O>[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:27][CH2:24][CH2:11][CH2:1][CH2:2][CH2:3][CH:33]=[CH2:34])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:27][CH2:24][CH2:3][CH2:2][CH2:1][CH2:11][CH2:16][CH:33]=[CH2:34])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 2

HCID 14439127HCID 14439127, compoundHCID 198347485-Decyl-2-(4-(hept-6-enyloxy)phenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Vinyl-terminated phenyl pyrimidines with different spacer lengths were synthesized from 4-(5-decylpyrimidin-2-yl)phenol for siloxane coupling to 1,2 polybutadiene. A general procedure for this synthesis is as follows: 4-(5-decylpyrimidin-2-yl)phenol (1.89 grams, 6.05 mmols), a bromoalkene (7-bromo hept-1-ene, 8-bromooct-1-ene or 10-bromododec-1-ene, 8 mmol) and Cs2CO3 (2.56 grams, 8 mmols) were stirred at room temperature in 40 mL of dimethyl formamide overnight, resulting in near-quantitative conversion to the ether (Scheme 3), monitored by thin layer chromatography. The reaction mixture was extracted three times with 50 mL of dichloromethane. The organic extracts were washed three times with water and dried with MgSO4. The crude product was recrystallized in hot 95% ethanol, resulting in analytically pure white crystals of 5-decyl-2-(4-(hept-6-enyloxy)phenyl)pyrimidine, 5-decyl-2-(4-(oct-7-enyloxy)phenyl)pyrimidine, -decyl-2-(4-(dec-9-enyloxy)phenyl)pyrimidine (1.20 g, 2.09 g, 1.69 g AND 48.0%, 83.6%, 66.02% overall yield, respectively).

Workup

  1. customVinyl-terminated phenyl pyrimidines with different spacer lengths
  2. customwere synthesized from 4-(5-decylpyrimidin-2-yl)phenol for siloxane coupling to 1,2 polybutadiene
  3. extractionThe reaction mixture was extracted three times with 50 mL of dichloromethane
  4. washThe organic extracts were washed three times with water
  5. dry with materialdried with MgSO4
  6. customThe crude product was recrystallized in hot 95% ethanol

Sources & evidence

ORD record
ord-39560a42cee9448f8d9d228d3cfc61ff
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08956705B2

Reaction notes

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