3,4-dihydro-2H-pyran → HCID 12966956, compound

HRID 2254550Notes

Reaction equation

HRID 2254550 reaction equation
[OH:1][C@@H:2]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])/[CH:3]=[CH:4]/[C@H:5]1[C@H:12]([O:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:11][C@H:10]2[C@@H:6]1[CH2:7][C:8](=[O:28])[O:9]2.[O:36]1[CH:41]=[CH:40][CH2:39][CH2:38][CH2:37]1>C(Cl)Cl>[C:21]1([C:18]2[CH:17]=[CH:16][C:15]([C:14]([O:13][C@@H:12]3[CH2:11][C@H:10]4[C@H:6]([CH2:7][C:8](=[O:28])[O:9]4)[C@H:5]3/[CH:4]=[CH:3]/[C@@H:2]([O:1][CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][O:36]3)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])=[CH:20][CH:19]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 12966955HCID 12966955, compound

Product 1

HCID 12966956HCID 12966956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 3S-hydroxy compound (4a) (4.58 g) was dissolved into methylene chloride (100 ml), and reacted with dihydropyran in the presence of a catalytic amount of p-toluenesulfonic acid-1H2O. After a usual work-up, the reaction mixture was column-chromatographed to give the title compound (5). Yield: 5.03 g.

Workup

  1. customAfter a usual work-up, the reaction mixture was column-chromatographed

Sources & evidence

ORD record
ord-3851f5cc2d3741569c0d23e125f5db85
Source dataset
uspto-grants-1993_08
Patent number
US05236907

Reaction notes

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