Acetic Anhydride → HCID 15723375, compound

HRID 654955Notes

Reaction equation

HRID 654955 reaction equation
C([Li])(C)(C)C.CCCCCC.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.[CH3:28][Si:29]([CH3:38])([CH3:37])[C:30]1[O:34][CH:33]=[C:32]([CH:35]=[O:36])[CH:31]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>O1CCCC1>[C:39]([O:36][CH:35]([C:32]1[CH:31]=[C:30]([Si:29]([CH3:38])([CH3:37])[CH3:28])[O:34][CH:33]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)(=[O:41])[CH3:40]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 8058HexaneHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 19885943HCID 19885943, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 15723375HCID 15723375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tert-butyl lithium (a 1.7M solution in hexane (1.27 ml, 2.16 mmol) was added to a -78° solution of 1-bromo-5-(1-naphthyl)-pentane (300 mg, 1.08 mmol) in tetrahydrofuran (2 ml) under nitrogen. After stirring for 30 minutes at -78°, a solution of 5-trimethylsilyl-3-furaldehyde (182 mg, 1.08 mmol) in tetrahydrofuran (0.5 ml) was added and the solution was stirred 2 hours at room temperature. Acetic anhydride (20 mg, 0.2 mmol) was added and the solution stirred at room temperature overnight. The reaction was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave an oil. Purification of the crude material by preparative TLC (developed with 10% ethyl ether/hexane) gave the title compound as a yellow oil.

Workup

  1. stirringthe solution was stirred 2 hours at room temperature
  2. stirringthe solution stirred at room temperature overnight
  3. customThe reaction was quenched with water
  4. extractionExtraction (ethyl ether) and evaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil
  7. customPurification of the crude material by preparative TLC (developed with 10% ethyl ether/hexane)

Sources & evidence

ORD record
ord-68b4862b99ef4d6c9104ba0d73968648
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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