Pyridine → HCID 53755102, compound

HRID 1608565Notes

Reaction equation

HRID 1608565 reaction equation
[OH:1][CH:2]1[C:13]2[C:14](=[O:15])[C:9]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])([CH2:10][CH2:11][CH:12]=2)[C:8]#[C:7][CH:6]=[CH:5][C:4]#[C:3]1.N1C=CC=CC=1.[O:30]([CH2:37][C:38](Cl)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.CCOCC>[O:30]([CH2:37][C:38]([O:1][CH:2]1[C:13]2[C:14](=[O:15])[C:9]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])([CH2:10][CH2:11][CH:12]=2)[C:8]#[C:7][CH:6]=[CH:5][C:4]#[C:3]1)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 69703Phenoxyacetyl chlorideHCID 54135319HCID 54135319, compound

Product 1

HCID 53755102HCID 53755102, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 6 (175 mg, 0,533 mmol) in 10 mL tetrahydrofuran was added pyridine (0.20 mL, 2.47 mmol) and phenoxyacetyl chloride (0.17mL, 1.23 mmol) and stirred for 15 h. The solution was diluted with ether and washed with water and saturated bicarbonate. The organic fraction was dried over MgSO4 and concentrated and the residue chromatographed over silica gel (10:1 hexane/ethyl acetate) to give 8-[(phenoxymethyl)carbonyloxy]-1-(t-butyldimethylsilyloxy)-bicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-13-one (11a) (184 mg, 75%).

Workup

  1. washwashed with water and saturated bicarbonate
  2. dry with materialThe organic fraction was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue chromatographed over silica gel (10:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e3ffe04072b743248406fd73e3d78534
Source dataset
uspto-grants-1995_03
Patent number
US05395849

Reaction notes

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