1-(Tributylstannyl)methanol → HCID 21220903, compound

HRID 1584800Notes

Reaction equation

HRID 1584800 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[OH:13][CH2:14][Sn](CCCC)(CCCC)CCCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:13][CH2:14][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1

Participants

5

Reactant 2

HCID 41935931-(Tributylstannyl)methanolHCID 212208405-Bromo-1-benzofuran-7-carbaldehyde

Product 1

HCID 21220903HCID 21220903, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-benzofuran-7-carbaldehyde (2.02 g), hydroxymethyltributyltin (4.29 g) and tetrakis(triphenylphosphine palladium (O) (1.03 g) in dry 1,4-dioxan (8 ml) was heated at reflux for 18 h. A further portion of catalyst (203 mg) was added and heating continued for 4 h. The reaction mixture was allowed to cool, and the solution was purified by FCC eluted with hexane:ethyl acetate (1:1) to give the title compound as yellow oil (0.95 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureheating
  4. temperatureto cool
  5. customthe solution was purified by FCC
  6. washeluted with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-82ede1bd2c714345a3a9ffaa9d90ed3e
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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