Tetrahydrofuran → HCID 86719448, compound

HRID 1481635Notes

Reaction equation

HRID 1481635 reaction equation
C1COCC1.[CH2:6]([Si:9]([CH2:24][CH:25]=[CH2:26])([CH2:21][CH:22]=[CH2:23])[CH2:10][CH2:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1)[CH:7]=[CH2:8].[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO>[CH2:24]([Si:9]([CH2:6][CH:7]=[CH2:8])([CH2:21][CH:22]=[CH2:23])[CH2:10][CH2:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1)[CH:25]=[CH2:26]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86719446HCID 86719446, compound

Product 1

HCID 86719448HCID 86719448, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

THF (25 ml) and methanol (MeOH) (25 ml) were added to 4-{3-(triallylsilyl)propyl}benzaldehyde (4) (11.0 g, 36.9 mmol) under a nitrogen atmosphere, the mixture was cooled to around 0° C. with ice, NaBH4 (2.8 g, 73.8 mmol) was added thereto, and the mixture was stirred for 3 hours. An aqueous solution of saturated sodium hydrogen carbonate was added to the reaction mixture. The aqueous layer was extracted with diethyl ether, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under a reduced pressure to give a crude product. The crude product was purified by separating by silica gel column chromatography (elution solvent: n-hexane/ethyl acetate=5/1) to give 4-{3-(triallylsilyl)propyl}benzyl alcohol (5) (yield amount: 9.2 g, yield: 84%), as shown in the following chemical reaction formula.

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. washthe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under a reduced pressure
  7. customto give a crude product
  8. customThe crude product was purified
  9. customby separating by silica gel column chromatography (elution solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-f5126a0f3b634326af046b74fed61e1c
Source dataset
uspto-grants-2016_08
Patent number
US09409929B2

Reaction notes

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