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

HRID 6060Notes

Reaction equation

HRID 6060 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

M)d) 1.5 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one were dissolved in 8 ml of DMF. 0.85 g of t-butyldimethylchlorosilane in 4 ml of DMF were then added dropwise. The mixture was stirred for 48 hours. The reaction mixtures was poured in to 100 ml of ether and washed with 1N hydrochloric acid. The organic phase was dried, filtered and evaporated. The material obtained was chromatographed on silica gel. There was 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-butyl).

Workup

  1. customThe reaction mixtures
  2. washwashed with 1N hydrochloric acid
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe material obtained
  7. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-22f7dc4741844f499aa6a903ab0faa86
Source dataset
uspto-grants-1993_09
Patent number
US05246960

Reaction notes

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