4-Chlorophenol → HCID 58579933, compound

HRID 2059857Notes

Reaction equation

HRID 2059857 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[CH2:12][Sn:13]([CH3:16])([CH3:15])[CH3:14]>C1COCC1.CCOC(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][Sn:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 13643086(Chloromethyl)(trimethyl)stannane

Product 1

HCID 58579933HCID 58579933, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (140 mg, 5.83 mmol) in anhydrous THF (150 mL) under N2 at RT was added dropwise 4-chlorophenol (738 mg, 5.74 mmol). After stirring the mixture at RT for 15 min, (chloromethyl)trimethylstannane (350 mg, 1.64 mmol) in anhydrous THF (5 mL) was added and the reaction was stirred at RT for 18 hours. The mixture was diluted with EtOAc (50 mL) and was washed with aqueous 1.0 N NaOH (3×60 mL). The EtOAc layer was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (silica gel/hexane, using LC-MS to identify fractions containing the desire product) to afford ((4-chlorophenoxy)methyl)-trimethylstannane 8A (457 mg, 87% yield). 1H NMR (400 MHz, Chloroform-D) δ ppm 7.03 (2H, d, J=8.78 Hz), 6.67 (2H, d, J=9.03 Hz), 3.94 (2H, s), 0.00 (9H, s).

Workup

  1. stirringthe reaction was stirred at RT for 18 hours
  2. washwas washed with aqueous 1.0 N NaOH (3×60 mL)
  3. dry with materialThe EtOAc layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (silica gel/hexane
  6. additioncontaining the desire product)

Sources & evidence

ORD record
ord-5cf8148f517342e29d612b375dca2982
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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