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1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane → HCID 178494055, compound

HRID 633595
Notes
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Reaction equation

HRID 633595 reaction equation
Br[C:2]1[CH:17]=[C:16]([S:18]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:15]=[CH:14][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]1.C[C:27]12CC3(C)P(C4C=CC=CC=4)[C:33](C)([CH2:35][C:29]([CH3:45])(O3)O1)[O:34]2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:27][O:34][C:33]1[N:11]=[CH:8][CH:7]=[C:29]2[C:45]([C:2]3[CH:17]=[C:16]([S:18]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)(=[O:20])=[O:19])[CH:15]=[CH:14][C:3]=3[O:4][C@H:5]3[CH2:10][CH2:9][C@H:8]([N:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]3)=[CH:22][N:21]([CH3:25])[C:35]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 534277901,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantaneHCID 178484115HCID 178484115, compound

Product 1

HCID 178494055HCID 178494055, compoundYield 341.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of Example 144B (60 mg, 0.14 mmol) and Example 59A (40.1 mg, 0.14 mmol) was degassed under argon. To this mixture was added dioxane (8 mL) followed by degassing with argon. To this mixture was added potassium phosphate, dibasic (109 mg, 0.626 mmol) and water (2.000 mL) followed by degassing with argon. To this mixture was added 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (6.91 mg, 0.024 mmol) and then immediately tris(dibenzylideneacetone)dipalladium (0) (8.92 mg, 9.74 μmol) followed by degassing with argon. The reaction mixture was heated at 100° C. for 1 hour. The mixture was cooled to ambient temperature and partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated to provide the title compound (0.042 g, 59% yield)

Workup

  1. customby degassing with argon
  2. additionTo this mixture was added potassium phosphate, dibasic (109 mg, 0.626 mmol) and water (2.000 mL)
  3. customby degassing with argon
  4. customby degassing with argon
  5. temperatureThe mixture was cooled to ambient temperature
  6. custompartitioned between saturated aqueous sodium chloride and ethyl acetate
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d3b156b009b74979a593bb0e8ca551bd
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321764B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes