Methanol → HCID 178455054, compound

HRID 1007955Notes

Reaction equation

HRID 1007955 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 was added N-benzyl-N-[4-(2,4-bis{[tert-butyl (dimethyl)silyl]oxy}phenyl)cyclohexylidene]amine (4.00 g) and tetrahydrofuran (480 ml) followed by methanol (120 ml). To the solution was added sodium borohydride (1.16 g) 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) 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 title compound (2.09 g, 54%) as a cream solid. 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. additionadded
  2. stirringAfter stirring for 10 min
  3. customthe layers were separated
  4. extractionthe aqueous layer extracted with dichloromethane (3×100 ml)
  5. washThe combined organic phases were washed with brine (50 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil
  9. customPurification via flash column chromatography (
  10. washSiO2, ethyl acetate/petroleum ether, gradient elution

Sources & evidence

ORD record
ord-3ab2e322dea441e08b59afbe19e7fd2f
Source dataset
uspto-grants-2004_09
Patent number
US06797731B2

Reaction notes

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