Methanol → HCID 178455054, compound

HRID 2307121Notes

Reaction equation

HRID 2307121 reaction equation
[CH2:1]([N:8]=[C:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[CH:17][C:16]=2[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.CO.[BH4-].[Na+]>C(OCC)C.[OH-].[Na+]>[CH2:1]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][Si:22]([C:25]([CH3:27])([CH3:28])[CH3:26])([CH3:23])[CH3:24])=[CH:17][C:16]=2[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])[CH2:13][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57232310N-benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylidene]amine

Product 1

HCID 178455054HCID 178455054, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added N-benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylidene]amine (4.00 g, 7.63 mmol) and anhydrous tetrahydrofuran (480 ml) followed by anhydrous methanol (120 ml). To the solution was added sodium borohydride (1.16 g, 30.5 mmol) and the reaction mixture stirred for 17 hr. The reaction mixture was then diluted with diethyl ether (600 ml) and aqueous sodium hydroxide (400 ml, 0.4M) was added. After stirring for 10 min, the layers were separated and the aqueous layer extracted with dichloromethane (3×100 ml). The combined organic phases were washed with brine (50 ml), dried over magnesium sulfate and concentrated in vacuo to give a yellow oil. Purification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, gradient elution using 1:9, 1:4, then 3:7, v/v) furnished the desired product as a cream coloured solid (2.09 g, 54%). δH(CDCl3) 0.01 (6H, s), 0.05 (6H, s), 0.80 (9H, s), 0.85 (9H, s), 1.18 (4H, m), 1.66 (2H, m), 1.87 (2H, m), 2.19 (1H, m), 2.68 (1H, M), 6.12 (1H, d), 6.23 (1H, dd), 6.77 (1H, d), 7.17 (5H, m).

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. additionwas added
  3. stirringAfter stirring for 10 min
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted with dichloromethane (3×100 ml)
  6. washThe combined organic phases were washed with brine (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a yellow oil
  10. customPurification via flash column chromatography (
  11. washSiO2, ethyl acetate/petroleum ether, gradient elution

Sources & evidence

ORD record
ord-311fd8051a7740ee89e7e508b1a29d98
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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