Propanal → HCID 58560673, compound

HRID 536780Notes

Reaction equation

HRID 536780 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][C@@H:14]2[C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[O:17][C:16]([CH3:27])([CH3:26])[O:15]2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH:33](=[O:36])[CH2:34][CH3:35]>C1COCC1>[CH2:1]([N:8]1[C:12]([CH:33]([OH:36])[CH2:34][CH3:35])=[C:11]([CH2:13][C@@H:14]2[C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[O:17][C:16]([CH3:26])([CH3:27])[O:15]2)[N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 527PropanalHCID 68001957HCID 68001957, compoundHCID 178418339Butyllithium

Product 1

HCID 58560673HCID 58560673, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzyl-4-(((4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazole (11 mg, 0.029 mmol) in THF (0.3 mL) at −78° C. was added n-butyllithium (21 μL, 1.6M) to produce a deep red solution. After 5 minutes, propanal (2.3 μL, 1.1 eq) was added and the mixture was warmed to room temperature. After standard workup, the title compound was isolated by silica gel chromatography (7 mg, 54%). 1H NMR (400 MHz, CDCl3) δ 7.35 (m, 3H), 7.30 (m, 2H), 5.35 (d, 7.6 Hz, 1H), 5.32 (d, 7.6 Hz, 1H), 4.52 (m, 1H), 3.86 (m, 1H), 3.64 (m, 1H), 3.03 (dd, 3.6 Hz, 16.4 Hz, 1H) 2.96 (dd, 6.8 Hz, 16.4 Hz, 1H), 1.55-1.17 (m, 12H), 1.27 (s, 3H), 1.25 (s, 3H), 1.00 (t, 7.3 Hz, 3H), 0.88 (t, 5.2 Hz, 3H). LRMS (APCI+) found 430.6, [M]+.

Workup

  1. customto produce a deep red solution

Sources & evidence

ORD record
ord-036cf6f2efbb456d9e15a0b92adb7638
Source dataset
uspto-grants-2014_10
Patent number
US08859615B2

Reaction notes

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