Pyridine → HCID 86752877, compound

HRID 965433Notes

Reaction equation

HRID 965433 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][O:4][C:5]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)[C:8]2([CH:15]3[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:17][CH:9]2[CH2:10]4)[CH2:14]3)[O:7][O:6]1.N1C=CC=CC=1.[C:33](Cl)(=[O:35])[CH3:34]>C(Cl)Cl>[F:26][C:2]([F:1])([F:25])[CH2:3][O:4][C:5]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:33](=[O:35])[CH3:34])[CH:19]=2)[C:8]2([CH:15]3[CH2:14][CH:13]4[CH2:12][CH:11]([CH2:10][CH:9]2[CH2:17]4)[CH2:16]3)[O:7][O:6]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86752878HCID 86752878, compound

Product 1

HCID 86752877HCID 86752877, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of dioxetane 3 (78.2 mg) in 15 mL of CH2Cl2 was placed under argon. Dry pyridine (40 μL, 2.3 eq.) was added followed after 5 min by 16.6 μL (1.1 eq.) of acetyl chloride. The reaction was judged complete by TLC after 2 hours, showing a new material which emitted blue-green light when the plate was heated. The volatiles were removed in vacuo leaving a yellow oil which was purified by preparative TLC using CH2Cl2 as eluent. A colorless oil (44 mg) was obtained: 1H NMR (CDCl3) δ 0.98 (m, 1H), 1.29 (m, 1H), 1.46-2.00 (m, 10H), 2.20 (br s, 1H), 2.325 (s, 3H), 3.06 (br s, 1H), 3.624 (dq, 1H), 3.938 (dq, 1H), 7.20 (dd, 1H), 7.28-7.64 (m, 3H).

Workup

  1. temperaturewas heated
  2. customThe volatiles were removed in vacuo
  3. customleaving a yellow oil which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-a9b9eacd75264af399fd24bd7afaf149
Source dataset
uspto-grants-1998_06
Patent number
US05773628

Reaction notes

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