Sodium Hydroxide → HCID 21272035, compound

HRID 1193487Notes

Reaction equation

HRID 1193487 reaction equation
[CH2:1]([C:3]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[OH:16])[CH3:2].Br[CH2:23][C:24]#[C:25][Si](C)(C)C.[OH-].[Na+]>CS(C)=O.O>[CH2:1]([C:3]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH2:25][C:24]#[CH:23])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 6425893-Bromo-1-(trimethylsilyl)-1-propyneHCID 21272036HCID 21272036, compound

Product 1

HCID 21272035HCID 21272035, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 1-ethyl-1,3,4,9-tetrahydro-8-hydroxy-pyrano[3,4-b]indole-1-acetate (6 g, 20.8 mmol), 3-bromo-1-trimethylsilyl-1-propyne [4.8 g, 25 mmol, prepared according to R. B. Miller, Synth. Comm., 2, 267 (1972)] and 2.5N--NaOH (10 mL, 25 mmol) in DMSO (60 mL) was heated under nitrogen for 30 minutes at 120° C. Upon cooling, the micture was diluted with 2 volumes of water, acidified with 2N--KHSO4 solution and extracted with ether. The extracts were dried (Na2SO4) and concentrated in vacuo. The residual oil (7 g) was flash-chromatographed (silica Merck-60, chloroform) to provide methyl 1-ethyl-1,3,4,9-tetrahydro-8-[(2-propynyl)oxy]-pyrano[3,4-b]indole-1-acetate (5.6 g, 83%) as an oil.

Workup

  1. temperatureUpon cooling
  2. extractionKHSO4 solution and extracted with ether
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residual oil (7 g) was flash-chromatographed (silica Merck-60, chloroform)

Sources & evidence

ORD record
ord-332707ad0d23436fbaa960f718fac26a
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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