Tris(furan-2-yl)phosphane → HCID 58934950, compound

HRID 855162Notes

Reaction equation

HRID 855162 reaction equation
O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26](I)[CH:27]=1)[O:24][CH:23]([C:29]([F:32])([F:31])[F:30])[C:22]([C:33]([O-:35])=[O:34])=[CH:21]2.[Br-].[CH2:37]([Zn+])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1COCC1>[CH2:37]([C:26]1[CH:27]=[C:18]([Cl:17])[CH:19]=[C:20]2[C:25]=1[O:24][CH:23]([C:29]([F:32])([F:31])[F:30])[C:22]([C:33]([OH:35])=[O:34])=[CH:21]2)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 86599478HCID 86599478, compoundHCID 178419772HCID 178419772, compound

Product 1

HCID 58934950HCID 58934950, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a chilled solution of 0.031 g (0.054 mmole) of bis(dibenzylideneacetone) palladium (0) and 0.025 g (0.107 mmol) of tri-2-furylphosphine in 5 mL degassed THF was added 0.500 g (0.535 mmol) of Wang resin 6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate followed by addition of 3.21 mL (1.605 mmol) of a 0.5 M soln of benzylzinc bromide. The reaction mixture was heated to 60° C. overnight. The reaction mixture was transferred and washed as follows: THF (×5), aqueous NH4Cl (×5), H2O (×5), MeOH (×5), and CH2Cl2 (×5). The resin was treated with 2 mL (TFA:CH2CL2, 1:1) for 30 minutes. The filtrate was collected and treatment was repeated. The resin was washed with CH2Cl2 (×2) and all filtrates were combined and concd. The resulting oil was purified using reverse phase chromatography to afford 0.024 g (12%) of a white crystalline solid: 1H NMR (CDCl3/400 MHz) 4.00 (s, 2H), 5.91 (q, 1H, J=7.1 Hz), 7.20 (m, 1H), 7.27 (m, 5H), 7.41 (d, 1H, J=2.5 Hz), 7.87 (s, 1H); 19F NMR (CDCl3/400 MHz) −79.4 (d, 3F, J=6.8 Hz); MS (ES+) 369 (M+1, 100); HRMS (ES−) m/z calcd for (M−H: C18H11O3ClF3) 367.0343, found 367.0333.

Workup

  1. washwashed
  2. additionThe resin was treated with 2 mL (TFA:CH2CL2, 1:1) for 30 minutes
  3. customThe filtrate was collected
  4. washThe resin was washed with CH2Cl2 (×2)
  5. customThe resulting oil was purified

Sources & evidence

ORD record
ord-b4341be9bd6d47d1b3d40ce4febabae7
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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