HCID 53755102, compound → HCID 54566074, compound

HRID 1608566Notes

Reaction equation

HRID 1608566 reaction equation
[O:1]([CH2:8][C:9]([O:11][CH:12]1[C:23]2[C:24](=[O:25])[C:19]([O:26][Si](C(C)(C)C)(C)C)([CH2:20][CH2:21][CH:22]=2)[C:18]#[C:17][CH:16]=[CH:15][C:14]#[C:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.C(Cl)(Cl)Cl>[O:1]([CH2:8][C:9]([O:11][CH:12]1[C:23]2[C:24](=[O:25])[C:19]([OH:26])([CH2:20][CH2:21][CH:22]=2)[C:18]#[C:17][CH:16]=[CH:15][C:14]#[C:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 53755102HCID 53755102, compound

Product 1

HCID 54566074HCID 54566074, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 11a in 26 mL of acetonitrile was added 4 mL of 48% HF. The solution was stirred for 72 h. The solution was diluted with chloroform and washed with water. The organic fraction was dried over MgSO4 and concentrated and the residue chromatographed over silica gel (5:1 hexane/ethyl acetate) to give 8-[(phenoxymethyl)carbonyloxy]-1-hydroxy-bicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-13-one (11b) (116 mg).

Workup

  1. washwashed with water
  2. dry with materialThe organic fraction was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue chromatographed over silica gel (5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0d5c787c7cfd481b974bbcdeb57bfa7c
Source dataset
uspto-grants-1995_03
Patent number
US05395849

Reaction notes

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