Tetrahydrofuran → HCID 86719448, compound

HRID 589228Notes

Reaction equation

HRID 589228 reaction equation
[CH2:1]([Si:4]([CH2:19][CH:20]=[CH2:21])([CH2:16][CH:17]=[CH2:18])[CH2:5][CH2:6][CH2:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)[CH:2]=[CH2:3].C1COCC1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO>[CH2:19]([Si:4]([CH2:1][CH:2]=[CH2:3])([CH2:16][CH:17]=[CH2:18])[CH2:5][CH2:6][CH2:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1)[CH:20]=[CH2:21]

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

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, to 4-{3-(triallylsilyl)propyl}benzaldehyde (4) (11.0 g, 36.9 mmol), THF (25 ml) and methanol (MeOH) (25 ml) were added and then cooled down to at around 0° C. with ice, and then NaBH4 (2.8 g, 73.8 mmol) was added and stirred for 3 hours. To the reacted mixture, saturated sodium bicarbonate aqueous solution was added. The obtained water layer was extracted with diethyl ether. The collected organic layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, obtaining a crude product. The crude product was separated and purified using silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1), obtaining 4-{3-(triallylsilyl)propyl}benzyl alcohol (38) represented by the following chemical reaction equation (yield: 9.2 g, yield (%): 84%).

Workup

  1. extractionThe obtained water layer was extracted with diethyl ether
  2. washThe collected organic layer was washed with saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customobtaining a crude product
  7. customThe crude product was separated
  8. custompurified

Sources & evidence

ORD record
ord-061e29b8b3c64e0eb5f1e2886e80390e
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

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