Thionyl Chloride → HCID 69055162, compound

HRID 2103005Notes

Reaction equation

HRID 2103005 reaction equation
COC[O:4][C:5]1[C:6]([CH3:23])=[C:7]2[C:15](=[C:16]([CH3:19])[C:17]=1[CH3:18])[O:14][C:10]1([CH2:13][CH2:12][CH2:11]1)[CH:9]([CH:20]=O)[C:8]2=[O:22].O=S(Cl)[Cl:26]>ClCCl>[Cl:26][CH:20]=[C:9]1[C:10]2([CH2:13][CH2:12][CH2:11]2)[O:14][C:15]2[C:7](=[C:6]([CH3:23])[C:5]([OH:4])=[C:17]([CH3:18])[C:16]=2[CH3:19])[C:8]1=[O:22]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86605476HCID 86605476, compound

Product 1

HCID 69055162HCID 69055162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-(methoxymethoxy)-5,7,8-trimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-3-carbaldehyde (2.0 g) in 20 mL of dichloromethane was added dropwise 5 mL of SOCl2. The reaction was allowed to stir at room temperature for 2 hr. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography eluted with 10-20% ethyl acetate in hexane to give 1.46 g of 3-(chloromethylene)-6-hydroxy-5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one, as a yellow solid. It is a mixture of two isomers with a ratio of about 3:1, as indicated by TLC analysis.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluted with 10-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4b378fff80b743d286e5180498a0b458
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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