8-Methylidene-1,4-dioxaspiro[4.5]decane → 3-[(3-Chlorophenyl)ethynyl]-8-methylene-1-oxa-2-azaspiro[4.5]dec-2-ene

HRID 2040864Notes

Reaction equation

HRID 2040864 reaction equation
[CH2:1]=[C:2]1[CH2:11][CH2:10][C:5]2([O:9]CCO2)[CH2:4][CH2:3]1.[Cl:12][C:13]1[CH:14]=[C:15]([C:19]#[C:20][C:21]2[CH2:25]C3(CCC(=O)CC3)O[N:22]=2)[CH:16]=[CH:17][CH:18]=1>>[Cl:12][C:13]1[CH:14]=[C:15]([C:19]#[C:20][C:21]2[CH2:25][C:5]3([CH2:4][CH2:3][C:2](=[CH2:1])[CH2:11][CH2:10]3)[O:9][N:22]=2)[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decaneHCID 566464673-[(3-Chlorophenyl)ethynyl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-one

Product 1

HCID 566464683-[(3-Chlorophenyl)ethynyl]-8-methylene-1-oxa-2-azaspiro[4.5]dec-2-ene

Procedure

The title compound was synthesized using the same methodology described for Compound 31a, but starting from the compound of Example 32 instead of 1,4-dioxaspiro[4.5]decan-8-one. After the usual work-up procedure, the residue was purified by means of automated flash chromatography (Horizon®TM-Biotage; gradient Petroleum Ether-Acetone EtOAc from 95:5 to 9:1) to give the title compound as a grey solid. Yield: 67.3%

Workup

  1. customThe title compound was synthesized
  2. customAfter the usual work-up procedure, the residue was purified by means of automated flash chromatography (Horizon®TM-Biotage; gradient Petroleum Ether-Acetone EtOAc from 95:5 to 9:1)

Sources & evidence

ORD record
ord-8accb33787e746d89d92d73953e8b050
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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