Diethyl Ether → (3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy-]6-undecyl-2H-pyran-2-one

HRID 703686Notes

Reaction equation

HRID 703686 reaction equation
[CH2:1]([C@H:7]1[C@@H:12]([OH:13])[CH2:11][C@@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27].CCOCC>CN(C=O)C>[CH2:1]([C@H:7]1[C@@H:12]([O:13][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32])[CH2:11][C@@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 11013671(3S,4S,6R)-3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

Product 1

HCID 22847451(3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy-]6-undecyl-2H-pyran-2-oneYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(1.O.d) 1.5 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one are dissolved in 8 ml of DMF. 0.85 g of t-butyldimethylchlorosilane in 4 ml of DMF are then added dropwise. The mixture is stirred for 48 hours. The reaction mixture is poured into 100 ml of ether and washed with 1N hydrochloric acid. The organic phase is dried, filtered and evaporated. The material obtained is chromatographed on silica gel. There are obtained 1.26 g of (3S,4S,6R)-tetrahydro-3-hexyl -4-[(t-butyldimethylsilyl)oxy-]6-undecyl-2H-pyran-2-one, MS: 411 (M+ -t-buytl),

Workup

  1. washwashed with 1N hydrochloric acid
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe material obtained
  6. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-7429671ce99340b599e8aab58d7cdd4b
Source dataset
uspto-grants-1991_01
Patent number
US04983746

Reaction notes

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