Water → HCID 17968139, compound

HRID 1373996Notes

Reaction equation

HRID 1373996 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([Si:11]([CH3:25])([CH3:24])[O:12][C:13]1[C:21]2[O:20][C:19]([CH2:22]Cl)=[CH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)([CH3:10])([CH3:9])[CH3:8].O>O1CCCC1.CN(C)C=O.C(O)(C)C>[C:7]([Si:11]([CH3:25])([CH3:24])[O:12][C:13]1[C:21]2[O:20][C:19](=[CH2:22])[CH2:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 3

HCID 962WaterHCID 17968135HCID 17968135, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 17968139HCID 17968139, compound

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.0M in tetrahydrofuran, 4.5 ml, 4.5 mmol) is added dropwise to a suspension of CrCl3 (1.4 g, 8.85 mmol) in tetrahydrofuran (10 ml), kept at 0° C. and the mixture is stirred for 15 minutes. The solution is then diluted with dimethylformamide (18 ml) and isopropanol (1.35 ml). tert-Butyldimethyl-(2-chloro-methylbenzofuran-7-yloxy)silane (15) (1.05 g, 3.54 mmol) in dimethylformamide (15 ml) is added to the solution obtained, kept at 0° C. The mixture is stirred at room temperature for 18 hours and then poured into water and extracted with pentane. The organic phase is dried over Na2SO4, filtered and concentrated under reduced pressure. A colorless liquid is obtained (0.78 g) which is used in the next step without further purification.

Workup

  1. customkept at 0° C.
  2. customobtained
  3. customkept at 0° C
  4. stirringThe mixture is stirred at room temperature for 18 hours
  5. extractionextracted with pentane
  6. dry with materialThe organic phase is dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customA colorless liquid is obtained (0.78 g) which
  10. customis used in the next step without further purification

Sources & evidence

ORD record
ord-4124b09778e44d758060b57ac3f9fa4f
Source dataset
uspto-grants-2007_01
Patent number
US07163957B2

Reaction notes

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