2H-Pyran, 2-ethynyltetrahydro- → HCID 57608474, compound

HRID 1618435Notes

Reaction equation

HRID 1618435 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=1)[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C:20]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)#[CH:21]>>[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:21]#[C:20][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:14]=1)[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 121609322H-Pyran, 2-ethynyltetrahydro-HCID 57608496HCID 57608496, compound

Product 1

HCID 57608474HCID 57608474, compound

Procedure

Sonogashira reaction of 106 with 2-ethynyltetrahydro-2H-pyran yielded tert-butyl 3-hydroxy-3-(3-((tetrahydro-2H-pyran-2-yl)ethynyl)phenyl)propylcarbamate (107) as dark brown oil. Yield (1.21 g, 83%): 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.27-7.35 (m, 3H), 4.87 (bs, 1H), 4.69-4.71 (m, 1H), 4.49-4.51 (m, 1H), 4.02-4.07 (m, 1H), 3.50-3.52 (m, 1H), 3.56-3.61 (m, 1H), 3.13-3.18 (m, 1H), 1.91-1.93 (m, 2H), 1.74-1.86 (m, 4H), 1.51 (m, 2H), 1.43 (s, 9H).

Sources & evidence

ORD record
ord-07c94a8c5912484e978b5602878553ed
Source dataset
uspto-grants-2014_07
Patent number
US08766007B2

Reaction notes

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