Chloroform → HCID 10387437, compound

HRID 860403Notes

Reaction equation

HRID 860403 reaction equation
[CH:1](Cl)(Cl)Cl.C=CC[CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C@@H:22]1[O:26][C@H:25]([C@@H:27]2[O:32][O:31][C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:29][CH2:28]2)[CH2:24][CH2:23]1>CO>[CH3:1][O:36][C:34]([CH2:33][C@H:30]1[O:31][O:32][C@H:27]([C@H:25]2[O:26][C@H:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]/[CH:15]=[CH:14]\[CH:13]=[CH:12]/[CH2:11][CH2:10][CH:9]=[CH2:8])[CH2:23][CH2:24]2)[CH2:28][CH2:29]1)=[O:35]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 71720233HCID 71720233, compound

Product 1

HCID 10387437HCID 10387437, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

colorless oil; [α]D25 −50.8° (c 0.39, CHCl3); IR (film) 1745, 1640, 1200, 1060 cm−1; UV (MeOH) λmax235 (ε=22000) nm- 1H NMR (CDCl3) 6.25 (m, 2H, H-18 and H-19), 5.82 (ddt, J=16.9, 10.3, 6.6 Hz, 1H, H-23), 5.44 (m, 2H, H-17 and H-20), 5.03 (ddd, J=16.9, 1.7, 1.6 Hz, 1H, H-24), 4.97 (bd, J=10.3 Hz, 1H, H-24), 4.54 (dddd, J=11.1, 7.7, 5.9, 2.2 Hz, 1H, H-3), 4.06 (ddd, J=11.1, 5.4, 2.4 Hz, 1H, H-6), 3.87 (m, 2H, H-7 and H-10), 3.69 (s, 3H, CH30-), 2.47 (dd, J=15.6, 7.7 Hz, 1H, H-2), 2.36 (dd, J=15.6, 5.9 Hz, 1H, H-2), 2.28 (bdd, J=14.7, 7.4, 2H, H-21), 2.15 (m, 2H, H-16), 2.13 (m, 2H, H-22), 1.99 (m, 1H, H-9), 1.95 (m, 1H, H-8), 1.92 (m, 1H, H-4eq), 1.77 (m, 2H, H-5ax and H-8), 1.70 (m, 1H, H-5eq), 1.58 (m, 1H, H-11),1.54 (m, 1H, H-4ax), 1.42 (m, 1H, H-9), 1.34 (m, 1H, H-11), 1.33 (m, 1H, H-12), 1.30 (m, 6H, H-13, H-14 and H-15), 1.28 (in, 1H, H-12); 13C NMR (CDCl3) 170.4 (s, C-1), 138.2 (d, C-23), 132.4 (d, C-17), 130.8 (d, C-20), 124.0 (d, C-19), 123.4 (d, C-18), 114.7 (t, C-24), 83.8 (d, C-6), 79.9 (d, C-10), 78.5 (d, C-7), 77.6 (d, C-3), 51.9 (q, CH3O—), 38.4 (t, C-2), 35.6 (t, C-11), 33.7 (t, C-22), 31.7 (t, C-9), 29.6 (t, C-13)*, 29.5 (t, C-14)*, 29.2 (t, C-15)*, 29.1 (t, C-4), 27.7 (t, C-8), 27.5 (t, C-16), 26.8 (t, C-21), 26.0 (t, C-12), 25.2 (t, C-5); EIMS (70 eV) m/z (rel. int.) 420 (2), 402 (18), 261 (25), 219 (7), 159 (15), 143 (36), 135 (29), 121 (41), 67 (100); HREIMS m/z 420.2865, C25H4005 requires m/z 420.2876.

Sources & evidence

ORD record
ord-3f62fdbb56f34e6d81074c9dbfc9489b
Source dataset
uspto-grants-2006_12
Patent number
US07153885B2

Reaction notes

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