Tetrahydrofuran → HCID 86642701, compound

HRID 2061064Notes

Reaction equation

HRID 2061064 reaction equation
[CH3:1][C:2]([N+:8]([O-:10])=[O:9])([CH3:7])[CH2:3][CH2:4][CH2:5][I:6].[CH3:11][P:12]([CH3:14])[CH3:13].C1COCC1>CC(=O)CC>[I-:6].[CH3:11][P+:12]([CH3:14])([CH3:13])[CH2:5][CH2:4][CH2:3][C:2]([CH3:7])([N+:8]([O-:10])=[O:9])[CH3:1]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 68983TrimethylphosphineHCID 99430631-Iodo-4-methyl-4-nitro-pentane

Product 1

HCID 86642701HCID 86642701, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

To a 100 mL round bottomed flask was added 4-methyl-4-nitropentyl iodide (2.0 g, 7.78 mmol), 2-butanone (20 mL) and a 1 M solution of trimethylphosphine in THF (15.5 mL, 2 equiv, 15.5 mmol). This flask was placed into a stainless steel pressure vessel, sealed and heated at 100° C. for 4 days. The vessel was cooled and opened in a fumehood. The flask was removed and contained a white solid. The steel vessel contained solvent. The white solid was suspended in ethyl acetate (100 mL), filtered, rinsed with EA (2×50 mL) and dried under high vacuum to give a pale yellow solid (2.39 g, 93%). 1H NMR (D2O, 400 MHz): δ 1.62 (s, 6H), 1.84-1.88 (d, J=14.4, 9H), 2.10-2.14 (m, 2H), 2.20-2.28 (m, 2H). LRMS (ESI+) for C9H21NO2P+ (206.1); Found: 206 (M+).

Workup

  1. customThis flask was placed into a stainless steel pressure vessel
  2. customsealed
  3. temperatureThe vessel was cooled
  4. customThe flask was removed
  5. filtrationfiltered
  6. washrinsed with EA (2×50 mL)
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-0ba55fb885d147e89b46d9dbc09466eb
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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