HCID 68315038, compound → HCID 68315060, compound

HRID 2202142Notes

Reaction equation

HRID 2202142 reaction equation
CO[C:3]([C@@:5]12[C:11]([CH3:13])([CH3:12])[C@@H:8]([CH2:9][CH2:10]1)[CH:7]=[C:6]2[C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22]([CH3:30])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])=[CH:16][C:15]=1[O:31][CH3:32])=O.COC1C=C(C(C)(CCCCC)C)C=C(OC)C=1B1OC(C)(C)C(C)(C)O1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:32][O:31][C:15]1[CH:16]=[C:17]([C:22]([CH3:30])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])[CH:18]=[C:19]([O:20][CH3:21])[C:14]=1[C:6]1[C@@:5]2([CH3:3])[C:11]([CH3:13])([CH3:12])[C@@H:8]([CH:7]=1)[CH2:9][CH2:10]2

Participants

4

Reactant 2

HCID 68315038HCID 68315038, compoundHCID 68315188HCID 68315188, compound

Product 1

HCID 68315060HCID 68315060, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared by the general procedure described for compound 11a, using pinacol arylboronate 3 (mixed with 1) 0.755 g, camphor enol triflate 10a 0.5 g (1.76 mmol), Pd(PPh3)4 0.122 g (0.011 mmol) and t-BuNF 2.64 ml (2.64 mmol, 1M solution in THF) to give yellowish oil 0.525 g (75%), which solidified upon standing at −20° C. to give a white solid. mp 34-36° C.; 1H NMR (300 MHz, CDCl3) δ ppm 6.50 (s, 2H), 5.87 (d, J=3.27 Hz, 1H), 3.74 (s, 6H), 2.37 (t, J=3.46, 1H), 1.88 (m, 1H), 1.65 (m, 1H), 1.61 (m, 2H), 1.55 (m, 1H), 1.30 (s, 6H), 1.15 (m, 1H), 1.19-1.26 (m, 6H), 1.07-1.18 (m, 2H), 1.05 (s, 3H), 0.86 (t, J=6.71 Hz, 3H), 0.83 (s, 3H), 0.82 (s, 3H). Exact mass calculated for C27H42O2 m/e 398.32. found 398.79. Anal. calcd. for C27H42O2: C, 81.35; H, 10.62. Found: C, 81.08; H, 10.69.

Sources & evidence

ORD record
ord-b49f09751d4941c281ee435899cfde93
Source dataset
uspto-grants-2016_06
Patent number
US09365534B2

Reaction notes

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