1,4-Dioxaspiro[4.5]decan-8-one → 3,4-Dihydro-4-methylene-1H-2-benzopyran

HRID 2040899Notes

Reaction equation

HRID 2040899 reaction equation
[CH2:1]=C1CCC2(OCCO2)CC1.[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=O)[CH2:14][O:13]1.O1C2(CCC(=O)CC2)OCC1>>[CH2:1]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][O:13][CH2:14]1

Participants

4

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decaneHCID 123396483,4-dihydro-1H-2-benzopyran-4-one

Product 1

HCID 111710523,4-Dihydro-4-methylene-1H-2-benzopyranYield 69.8%

Procedure

This intermediate was prepared following the procedure described Compound 31a. As starting material isochroman-4-one replaced 1,4-dioxaspiro[4.5]decan-8-one. After the usual work-up procedure the residue was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 1:0 to 0:1) to give the title compound as a colorless oil. Yield: 69.8%.

Workup

  1. customThis intermediate was prepared
  2. customAfter the usual work-up procedure the residue was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 1:0 to 0:1)

Sources & evidence

ORD record
ord-4dd68c44738e483d9dca3f6548686b8b
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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