Dichloromethane → HCID 131721391, compound

HRID 382249Notes

Reaction equation

HRID 382249 reaction equation
C(OC1[O:42][C@H:41]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[C@@H:16]([O:17][C@@H:18]2[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]2[O:20][CH2:21][CH:22]=[CH2:23])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.[CH2:48]([Cl:50])Cl>[Zn+2].[Br-].[Br-]>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C@@H:18]2[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]2[O:20][CH2:21][CH:22]=[CH2:23])[C@@H:41]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[O:42][C@@H:48]1[Cl:50])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 10747064HCID 10747064, compound

Product 1

HCID 131721391HCID 131721391, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

To a solution of 2 (3.5 g, 5.17 mmol) in CH2Cl2 (10 mL) Cl2CHOCH3 (0.56 mL, 6.2 mmol) and ZnBr2 (100mg) were added under an Ar atmosphere. The mixture was stirred for 1 h, then concentrated and the residue was chromatographed on silica gel with pentane-EtOAc (6:4) to give 3 (396 mg, 85%), [α]D+93.4° (c 1.2, CHCl3); 1H NMR (CDCl3) δ 6.22 (s, 1H, J1,2=3.9 Hz, H-1), 5.80 (m, 1H, Hc), 5.56 (t, 1H, J3,4 and J2,3≈9.7 Hz, H-3), 5.31 (dd, 1H, J4′,3′=3.5 Hz, J4′,5′=0.8 Hz, H-4′), 5.20 (1H, Hb), 5.12 (1H, Ha), 4.93 (dd, 1H, H-2),4.86(dd, 1H, J2′,3′=10.2 Hz, H-3′), 4.58 (dd, 1H, J6a,6b=12.1 Hz, J5,6a=0.7 Hz, H-6a), 4.34 (d, 1H, J1′,2′=7.7 Hz, H-1), 4.29 (dd, 1H, J5,6b =4.2 Hz, H-6B),4.25-4.01 (m, 5H, Hd, He, H-5, H-6′a, H-6′b), 3.85-3.78 (m, 2H, H-4, H-5′), 3.42 (dd, 1H, H-2′). Calc'd for C27H37Cl16 (653.025) C, 49.66; H, 5.71, Cl, 5.43. Found C, 49.68, H, 5.68, Cl, 5.73.

Workup

  1. concentrationconcentrated
  2. customthe residue was chromatographed on silica gel with pentane-EtOAc (6:4)

Sources & evidence

ORD record
ord-cb543cd1dcb24fb3a89e68259822d42e
Source dataset
uspto-grants-2001_10
Patent number
US06310043B1

Reaction notes

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