Tetrahydrofuran → HCID 18792141, compound

HRID 1005500Notes

Reaction equation

HRID 1005500 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[F:12][C:13]([F:61])([C:51]([F:60])([F:59])[C:52]([F:58])([F:57])[C:53]([F:56])([F:55])[F:54])[CH2:14][CH2:15][CH2:16][N:17]([CH2:35][CH2:36][CH2:37][C:38]([F:50])([F:49])[C:39]([F:48])([F:47])[C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42])[C:18](=O)[CH2:19][CH2:20][C:21]([F:33])([F:32])[C:22]([F:31])([F:30])[C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25]>O>[F:12][C:13]([F:61])([C:51]([F:59])([F:60])[C:52]([F:57])([F:58])[C:53]([F:54])([F:55])[F:56])[CH2:14][CH2:15][CH2:16][N:17]([CH2:18][CH2:19][CH2:20][C:21]([F:33])([F:32])[C:22]([F:30])([F:31])[C:23]([F:28])([F:29])[C:24]([F:25])([F:26])[F:27])[CH2:35][CH2:36][CH2:37][C:38]([F:50])([F:49])[C:39]([F:48])([F:47])[C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 18792149HCID 18792149, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 18792141HCID 18792141, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 250-ml 3-necked flask equipped with a stir bar, condenser, nitrogen inlet and an addition funnel was charged with LiAlH4 (1.3 g) and 20 ml THF. To the mixture was added a THF (30 ml) solution of N,N-bis(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)-4,4,5,5,6,6,7,7,7-nonafluoroheptanamide (20.6 g, 25.4 mmol) dropwise at RT. The resulting mixture was refluxed for 30 min. After being cooled, the mixture was carefully treated with water (3 ml) to decompose excess LiAlH4. Another 50 ml water were added and the mixture was extracted with ether (3×100 ml). The combined ether extracts were washed with water, dried over Na2SO4, concentrated to give a residue which was distilled to afford tris(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)amine, 17.5 g, yield 86%, bp 153-155° C./270 Pa absolute. 19F NMR (CDCl3) -81.8 (tt, J=10, 3 Hz, 9F), -115.2 (m, 6F), -125.3 (m, 6F), -126.7 (m, 6F) ppm. 1H NMR (CDCl3) 1.92 (m, 6H), 2.10 (m, 6H), 2.48 (t, J=6 Hz, 6H) ppm. 13C NMR (CDCl3) 18.3, 28.7 (t, J=23 Hz), 52.9, 108-123 (m) ppm. Anal. Calcd. for C21H18F27N: C, 31.63; H, 2.28; N, 1.76; F 64.33. Found: C, 31.49; H, 2.52; N, 1.77; F, 64.52. MS (m/e) 550 (M+ -C4F9 (CH2)2, 100%), 512 (0.4%), 462 (0.6%), 362 (0.8%), 290 (11.3%), 276 (1.9%), 219 (0.3%), 169 (3.9%), 119 (7.1%), 69 (23.7%).

Workup

  1. customA 250-ml 3-necked flask equipped with a stir bar, condenser, nitrogen inlet and an addition funnel
  2. temperatureThe resulting mixture was refluxed for 30 min
  3. temperatureAfter being cooled
  4. extractionthe mixture was extracted with ether (3×100 ml)
  5. washThe combined ether extracts were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give a residue which
  9. distillationwas distilled

Sources & evidence

ORD record
ord-a6a41f761702463fa66a162ebdfcbac4
Source dataset
uspto-grants-2000_04
Patent number
US06054615

Reaction notes

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