Hydrogen Bromide → HCID 53733392, compound

HRID 619985Notes

Reaction equation

HRID 619985 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][O:12][CH2:11]2)=O)=[CH:5][CH:4]=1.O1C=CCCC1.Br.BrC1CCCOC1.C(OCC)(=O)CC(OCC)=O.O1CCCC(C(C(OCC)=O)C(OCC)=O)C1.O=S(Cl)Cl.C1(OC)C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1COCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][O:12][CH2:11]2)=[CH:16][CH:17]=1

Participants

12

Reactant 9

HCID 260Hydrogen BromideHCID 7519AnisoleHCID 7761Diethyl MalonateHCID 80803,4-dihydro-2H-pyranHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 122510813-bromotetrahydro-2H-pyranHCID 21247805HCID 21247805, compoundHCID 21248101HCID 21248101, compound

Product 1

HCID 53733392HCID 53733392, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 23.4 g of 3-(p-methoxybenzoylmethyl)tetrahydropyran (obtainable by reaction of 2,3-dihydro-4H-pyran with HBr to give 3-bromotetrahydropyran, reaction with diethyl malonate to give diethyl tetrahydropyran-3-ylmalonate, hydrolysis, decarboxylation, reaction with SOCl2 to give tetrahydropyran-3-acetyl chloride, and reaction with anisole in the presence of AlCl3) in 500 ml of THF is hydrogenated on 5 g of 10% Pd/C at 40° and 1 bar until 0.2 mole of H2 has been taken up. The mixture is filtered, evaporated and 3-(2-p-methoxyphenylethyl)tetrahydropyran is obtained.

Workup

  1. customto give
  2. customto give
  3. customto give
  4. filtrationThe mixture is filtered
  5. customevaporated

Sources & evidence

ORD record
ord-39a12ffbe2af43f2b91f2815619f32b5
Source dataset
uspto-grants-1989_04
Patent number
US04818431

Reaction notes

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