Chloromethyl Methyl Ether → HCID 69054496, compound

HRID 2103003Notes

Reaction equation

HRID 2103003 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:17].[H-].[Na+].[CH2:21](Cl)[O:22][CH3:23]>C1COCC1>[CH3:21][O:22][CH2:23][O:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:7]1([CH2:8][CH2:9][CH2:10]1)[CH2:6][C:5]2=[O:17]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 69059851HCID 69059851, compound

Product 1

HCID 69054496HCID 69054496, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-Hydroxy-5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one (2.2 g) in 20 mL of THF at 0° C. was added sodium hydride (370 mg, 60% in mineral oil). After 5 min, MOM-Cl (0.96 mL) was added slowly to the reaction. After the reaction was complete, the mixture was extracted with ethyl acetate and was washed with water. The organic layer was separated and dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography eluted with 20% ethyl acetate in hexane to give 2.0 g of 6-(methoxymethoxy)--5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one as a yellow paste.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwas washed with water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bb4b47a7b73a44468879014fa6d201da
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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