Pyridine → HCID 66779249, compound

HRID 1970223Notes

Reaction equation

HRID 1970223 reaction equation
[CH2:1]([O:5][C:6]1[CH:36]=[CH:35][C:9]2[C:10]3[C:27]4([O:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH2:29][O:28]4)[C:11]=3[C:12]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])=[CH:16][C:13]=3[CH2:14][CH2:15][C:8]=2[CH:7]=1)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.Cl[C:44]([O:46][C:47]1[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=1)=[O:45]>C(Cl)Cl>[C:44](=[O:45])([O:46][C:47]1[CH:48]=[CH:49][C:50]([N+:53]([O-:55])=[O:54])=[CH:51][CH:52]=1)[O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:12]2[C:11]3[C:27]4([O:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH2:29][O:28]4)[C:10]=3[C:9]3[CH:35]=[CH:36][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][C:8]=3[CH2:15][CH2:14][C:13]=2[CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 667789362-{2-[(9-Butoxy-5',5'-dimethyl-6,7-dihydrospiro-[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethanol

Product 1

HCID 66779249HCID 66779249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of alcohol 11 (0.439 g, 0.89 mmol) and pyridine (0.25 g, 3.21 mmol) in CH2Cl2 (approximately 5 mL) was added to a solution of 4-nitrophenyl chloroformate (0.30 g, 1.49 mmol) in CH2Cl2 (25 mL) at room temperature, and the reaction mixture was stirred for 20 minutes at room temperature. Solvent was evaporated under reduced pressure, and the residue was separated by chromatography (Hex:ExOAc 4:1+1.5% of Et3N) to provide 0.317 g (0.48 mmol 80%) of 12 as and 0.113 g (0.23 mmol) of starting 11. 1H NMR: 8.25 (d, J=8.8 Hz, 2 H) 7.65 (dd, J=8.4, 2.0 Hz, 2 H), 7.35, (d, J=9.2, 2 H), 6.92-6.82 (m, 4 H), 4.43 (t, J=4.4 Hz, 2 H), 4.19 (t, J=6.4 Hz, 2 H), 3.98 (t, J=4.4 Hz, 2 H), 3.92 (m, 7 H), 3.22 (d, J=10.8 Hz, 2 H), 2.43 (d, J=10.8 Hz, 2 H), 1.75 (p, J=7.2 Hz, 2 H), 1.51 (six, J=7.6 Hz, 2 H), 1.21 (s, 3H), 1.19 (s, 3 H), 0.98 (t, J=−7.2 Hz, 3 H); 13C NMR: 159.9, 159.2, 155.7, 152.7, 150.0 147.4, 145.6, 131.77, 131.63, 125.5, 124.6, 123.4, 122.0, 119.8, 119.1, 116.25, 116.19, 112.2, 112, 15, 84.1, 79.4, 70.0, 69.1, 68.4, 70.0, 67.8, 37.1, 31.5, 30.8, 22.87, 22.79, 19.5, 14.1.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customthe residue was separated by chromatography (Hex:ExOAc 4:1+1.5% of Et3N)

Sources & evidence

ORD record
ord-feb2ac81c67b48c18ad4fe1d7a7f3541
Source dataset
uspto-grants-2013_04
Patent number
US08426649B2

Reaction notes

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