Benzoyl chloride → HCID 131718864, compound

HRID 275054Notes

Reaction equation

HRID 275054 reaction equation
[C:1]([O:9][C@H:10]1[CH2:16][C@H:15]2[N:17]([CH3:18])[C@H:12]([CH2:13][CH2:14]2)[C@H:11]1/[CH:19]=[CH:20]/C(OCC)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[PH:26](=[O:31])([O-:30])[O:27]C=C.[OH2:32].O.O.[F-].C([N+](CC[CH2:51][CH3:52])(CCCC)CCCC)CCC.[C:53]1([C:59](Cl)=[O:60])C=CC=CC=1>>[C:1]([O:9][C@H:10]1[CH2:16][C@H:15]2[N:17]([CH3:18])[C@H:12]([CH2:13][CH2:14]2)[C@H:11]1/[CH:19]=[CH:20]/[P:26]([O:27][O:32][CH2:51][CH3:52])([O:30][O:60][CH2:59][CH3:53])=[O:31])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 7412Benzoyl chlorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 67807585HCID 67807585, compoundHCID 178476828HCID 178476828, compound

Product 1

HCID 131718864HCID 131718864, compound

Procedure

Compound 2f was prepared in an identical fashion to ester 2e by simply substituting the anion prepared from (tetraethyl)methylenediphosphonate for the Wittig reagent used above. The resulting vinyl phosphonate was then treated sequentially with TBAF·3H2O and PhCOCl as described in Example 7 to yield 2f: [α]22D =14.4° (c=0.355 g/100 mL, CHCl3); IR (thin film) 2958, 2931, 1714, 1452, 1315, 1275, 1114, 1051, 1026, 1798, 715 cm-1 ; 1H NMR (CDCl3) δ=1.09, 1.21 (each 3H, t, J=7.1 Hz, P(OEt)2), 1.65-1.70 (2H, m, H-6, H-7), 1.82-1.88 (1H, m), 1.99-2.12 (3H, m, H-6, H-7, H-4 ), 2.15 (3H, s, N-Me ), 2.83-2.88 (1H, m, H-2 ), 3.05-3.08 (1H, m, H-5), 3.22 (1H, br s, H-1), 2.72-4.00 (4H, m, P(OEt)2), 5.19 (1H, ddd, J=12.1, 6.8, 6.3 Hz, H-3), 5.59 (1H, dd, J=17.3, 21.6 Hz, =CH(P(OEt)2), 7.17 (1H, ddd, J=2.19, 17.3, 9.4 Hz, CH=CHP(O)(OEt)2), 7.32-7.51 (3H, m, Ar), 7.91-7.93 (2H, m, Ar); 13C NMR (CDCl3) δ16.17 (d, JC-P= 7.5 Hz), 25.05, 26.04, 29.58, 5.53, 41.11, 50.10 (d, JC-P= 22.1 Hz) 61.33, (d, JC-P =7.9 Hz), 66.57, 68.85, 118.33 (d, JC-P =184.7 Hz), 128.18, 29.47, 130.08, 132.86, 152.91, 165.67; MS (m/z) 407 (M+), 287, 286, 270 (base), 205, 148, 147, 123, 121, 105, 97, 94, 91, 83, 82, 81, 77, 76.

Sources & evidence

ORD record
ord-5ac2b591e0ee4e26af9ddcc3bab466e5
Source dataset
uspto-grants-1995_02
Patent number
US05391744

Reaction notes

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