Aluminium lithium hydride → HCID 58881982, compound

HRID 2075782Notes

Reaction equation

HRID 2075782 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[CH:10][C:11]([Se:17][Se:18][C:19]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:20]=2[C:21](O)=[O:22])=[C:12]([CH:16]=1)[C:13](O)=[O:14]>O1CCCC1>[CH:26]1[C:25]([F:28])=[CH:24][C:20]([CH2:21][OH:22])=[C:19]([Se:18][Se:17][C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:16][C:12]=2[CH2:13][OH:14])[CH:27]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58881974HCID 58881974, compound

Product 1

HCID 58881982HCID 58881982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium aluminum hydride (0.89 g, 23 mmol) in dry tetrahydrofuran (20 mL) under argon at room temperature, 2,2′-diselenobis(5-fluorobenzoic acid) (116) (2.05 g, 4.70 mmol) dissolved in 10 mL of dry tetrahydrofuran was added dropwise. After refluxing for 50 minutes, the mixture was quenched with 20 mL of water and extracted with ethyl acetate. The aqueous solution was left sitting overnight with consequent precipitation of 815 mg (42%) of 137 as yellow needles with mp 112° C. IR (KBr) 3214 (broad), 1577, 1016, 874, 814 cm−1; 1H NMR (300 MHz) δ 7.52 (dd, J=8.2 Hz, 5.6 Hz, 1H), 7.24 (dd, J=9.8 Hz, 1H), 6.89 (dt, J=8.2 Hz, 3.1 Hz, 1 H), 4.69 (s, 2H), 2.06 (br s, 1H); mass spectrum, m/z (relative intensity) 410 (10, M+), 188 (23), 123 (16), 96 (100), 75 (16). Exact mass calcd for C14H12O2F280Se: 409.9134. Found: 409.9132.

Workup

  1. additionwas added dropwise
  2. temperatureAfter refluxing for 50 minutes
  3. customthe mixture was quenched with 20 mL of water
  4. extractionextracted with ethyl acetate
  5. waitThe aqueous solution was left
  6. customsitting overnight with consequent precipitation of 815 mg (42%) of 137 as yellow needles with mp 112° C

Sources & evidence

ORD record
ord-85c91cdf2a30405d99659bb21f8c4273
Source dataset
uspto-grants-2011_04
Patent number
US07923442B2

Reaction notes

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