Tetrahydrofuran → HCID 22459796, compound

HRID 2185217Notes

Reaction equation

HRID 2185217 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7](C=O)[CH2:6][C:5]2([CH3:15])[CH3:14].O1[CH2:20][CH2:19][CH2:18]C1.C([Mg]Br)C.C(OCC)(=O)C>C(OCC)C.CCCCCC>[CH:18]1([CH:8]2[C:9]3[C:4](=[CH:3][C:2]([OH:1])=[CH:11][CH:10]=3)[C:5]([CH3:14])([CH3:15])[CH2:6][NH:7]2)[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 225688696-Hydroxy-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-2-carbaldehyde2×HCID 178418443HCID 178418443, compound

Product 1

HCID 22459796HCID 22459796, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
55 °C

Procedure

A stirred, cooled (0° C.)solution of 6-hydroxy-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-2-carbaldehyde (Intermediate 20, 2.3 g, 11.21 mmol) anhydrous tetrahydrofuran (40 mL) under argon was treated with titanium tetra-iso-propoxide (8.28 mL, 28 mmol) followed by 3M solution of ethyl magnesium bromide in diethyl ether (18.7 mL) and the reaction mixture was then heated at 55° C. overnight. It was then cooled in an ice-bath, quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a yellow oily solid. Flash column chromatography over silica gel (230-400 mesh) using 10-20% ethyl acetate in hexane as the eluent afforded the title compound as a pale yellow solid (1.55 g, 63%).

Workup

  1. temperatureIt was then cooled in an ice-bath
  2. customquenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a yellow oily solid

Sources & evidence

ORD record
ord-0c56d2b8a0814004b55401b824a05175
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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