Tetrahydrofuran → HCID 23119393, compound

HRID 1819507Notes

Reaction equation

HRID 1819507 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH3:13])[O:12][CH2:11][CH2:10][O:9]1.CN(C)CCN(C)[CH2:19][CH2:20]N(C)C.C([Li])CCC.[Cl-].[NH4+].[CH2:33]1[CH2:37][O:36][CH2:35][CH2:34]1>CCCCCC>[F:1][C:2]1[C:7]([CH:35]([OH:36])[CH2:34][CH2:33][CH2:37][CH2:19][CH3:20])=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH3:13])[O:9][CH2:10][CH2:11][O:12]1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 18196PentamethyldiethylenetriamineHCID 25517Ammonium ChlorideHCID 11252353HCID 11252353, compoundHCID 178418339Butyllithium

Product 1

HCID 23119393HCID 23119393, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a THF (48 mL) solution of 2-(2-fluorophenyl)-2-methyl-1,3-dioxolane (6.0 g) and N,N,N′,N″,N″-pentamethyldiethylenetriamine (8.0 mL) was added 1.58 M hexane solution of n-butyl lithium (25.3 mL) dropwise at −78° C. After the reaction mixture was stirred for 1 h, n-hexylaldehyde (5.88 mL) was added into the reaction mixture. After the reaction mixture was stirred for additional 1 h at −78° C., a saturated ammonium chloride aqueous solution was added into the reaction mixture. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by Colum chromatography (hexane:ethyl acetate=4:1) to obtain the compound (16) 6.9 g.

Workup

  1. stirringAfter the reaction mixture was stirred for additional 1 h at −78° C.
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water, and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe obtained residue was purified by Colum chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a2e72493d574481485611dc7c6f48eec
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

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