Ethyl Acetate → HCID 15718043, compound

HRID 1085638Notes

Reaction equation

HRID 1085638 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][S:11]([C:14]1[C:15]([O:40][CH2:41][CH2:42][CH3:43])=[C:16]([O:38][CH3:39])[CH:17]=[C:18]([C:20](=[O:37])[CH2:21][CH2:22][C:23]([C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)=[O:24])[CH:19]=1)(=[O:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].C(OCC)(=O)C>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][S:11]([C:14]1[C:15]([O:40][CH2:41][CH2:42][CH3:43])=[C:16]([O:38][CH3:39])[CH:17]=[C:18]([CH:20]([OH:37])[CH2:21][CH2:22][C:23](=[O:24])[C:25]2[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=2)[CH:19]=1)(=[O:13])=[O:12])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 15718036HCID 15718036, compoundHCID 16710494Lithium tri-tert-butoxyaluminohydride

Product 1

HCID 15718043HCID 15718043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(5-(2-t-butyldimethylsilyloxyethylsulfonyl)-4-n-propoxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butan-1,4-dione (1.076 g, 1.70 mmole) at 0° C. in dry THF (40 mL) under nitrogen was treated with lithium tri-t-butoxyaluminum hydride (500 mg, 2 mmole), and the mixture was stirred at 0° C. for 1 hour. The reaction was allowed to warm to room temperature and stirred for 3 hours. The mixture was poured into ethyl acetate (500 mL), and the ethyl acetate solution was washed with 1 N HCl (2×100 mL), water and brine, dried over anhydrous MgSO4, and evaporated to dryness. The crude product was purified by flash column chromatography on SiO2 and eluted with 40% hexane ethyl acetate (3:2 v/v) to provide the pure title product as a thick syrup.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 3 hours
  3. washthe ethyl acetate solution was washed with 1 N HCl (2×100 mL), water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated to dryness
  6. customThe crude product was purified by flash column chromatography on SiO2
  7. washeluted with 40% hexane ethyl acetate (3:2 v/v)

Sources & evidence

ORD record
ord-b33aa17001f64e679cd4ed7afac440fd
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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