Hydrochloric Acid → HCID 18402480, compound

HRID 1018813Notes

Reaction equation

HRID 1018813 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([Li])CCC.[O:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.Cl>O1CCCC1.CCCCCC>[O:14]1[CH2:15][CH:16]=[C:17]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418339Butyllithium

Product 1

HCID 18402480HCID 18402480, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

[lacuna] is added at −40° C. to 12.7 g of 4-bromophenol in 150 ml of tetrahydrofuran. At this same temperature, 100 ml of 1.6 M butyllithium in hexane are added to the reaction mixture, followed by addition of 8.1 g of 4-tetrahydropyranone. The reaction mixture is left stirring for 18 hours at room temperature and then hydrolysed with 1 N hydrochloric acid. The resulting mixture is extracted several times with diethyl ether, the organic phase is dried over magnesium sulphate and the solvents are evaporated off under reduced pressure. The solid obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/ethyl acetate mixture varying from 90/10 to 80/20 (v/v).

Workup

  1. waitThe reaction mixture is left
  2. extractionThe resulting mixture is extracted several times with diethyl ether
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. customthe solvents are evaporated off under reduced pressure
  5. customThe solid obtained
  6. customis purified by chromatography on a column of silica gel
  7. washeluting with a cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-ecc9edb5637e41029d49bc29ca0d8bfc
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

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