Tributylphosphine → HCID 66685272, compound

HRID 922297Notes

Reaction equation

HRID 922297 reaction equation
[OH:1][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.[C:19]([CH:21]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)[CH2:22][C:23]([O:25][CH3:26])=[O:24])#[N:20].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[C:19]([CH:21]([C:27]1[CH:32]=[CH:31][C:30]([O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9](=[O:10])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:17][CH:18]=2)=[CH:29][CH:28]=1)[CH2:22][C:23]([O:25][CH3:26])=[O:24])#[N:20]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 60623767HCID 60623767, compoundHCID 66685605Methyl 3-cyano-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 66685272HCID 66685272, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a 100 mL of two neck RB flask was charged with 2-[4-(hydroxy methyl)phenoxy]-1-phenylethanone (2.5 g, 10.3 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (2.5 g, 12.4 mmol) in 50 mL of toluene. To this added tributylphosphine (3.33 g, 16.5 mmol) at 0° C. and added 1,1′-(Azodicarbonyl)dipiperidine (4.165 g, 16.5 mmol) portion wise over a period of 15 min at 0° C. After 12 h of stirring at RT, the mixture was diluted with n-hexane and stirred for 10 min. Solid formed was filtered off and the filtrate was concentrated to afford crude product which on trituration with ethyl acetate and pet ether gave pure product. (2.5 g yield: 56.1%); 1H NMR (300 MHz, DMSO-d6): δ 8.01-8.03 (d, 2H), 7.67-7.72 (t, 1H), 7.55-7.60 (t, 2H), 7.34-7.37 (d, 4H), 6.96-7.02 (t, 4H), 5.59 (s, 2H), 5.01 (s, 2H), 4.37-4.46 (m, 1H), 3.61 (s, 3H), 3.07-3.16 (m, 1H), 2.90-2.97 (m, 1H).

Workup

  1. stirringstirred for 10 min
  2. customSolid formed
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated
  5. customto afford crude product which on trituration with ethyl acetate and pet ether
  6. customgave pure product

Sources & evidence

ORD record
ord-91829a8190c441f89e188966bc044679
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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