Aluminium lithium hydride → HCID 57025985, compound

HRID 1284873Notes

Reaction equation

HRID 1284873 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]([F:41])([F:40])[CH2:11][C@H:12]([C@@H:14]1[C@:31]2([CH3:32])[C@H:17]([C@H:18]3[C@H:28]([CH2:29][CH2:30]2)[C@:26]2([CH3:27])[C:21]([CH2:22][C@@H:23]([O:33]C4CCCCO4)[CH2:24][CH2:25]2)=[CH:20][CH2:19]3)[CH2:16][CH2:15]1)[CH3:13]>CCOCC>[F:40][C:10]([F:41])([CH2:11][C@H:12]([C@@H:14]1[C@:31]2([CH3:32])[C@H:17]([C@H:18]3[C@H:28]([CH2:29][CH2:30]2)[C@:26]2([CH3:27])[C:21]([CH2:22][C@@H:23]([OH:33])[CH2:24][CH2:25]2)=[CH:20][CH2:19]3)[CH2:16][CH2:15]1)[CH3:13])[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57033897HCID 57033897, compound

Product 1

HCID 57025985HCID 57025985, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminium hydride (63 mg, 1.65 mmol) in ether (10 ml) the difluoroester (6) (1.40 g, 2.76 mmol) in ether (10 ml) was added and the mixture was stirred at 0° C. for 10 min and then stirred at room temperature for 10 min. The usual work-up (ether for extraction) gave a crude product, which was applied to a column of silica gel (100 g). Elution with n-hexane-ether (5:1) gave the alcohol (7) (1.13 g, 86%), viscous oil. 1H-NMR δ: 0.73 (3H, s, 18-H3), 1.03 (3H, s, 19-H3), 1.13 (3H, d, J=6 Hz, 21-H3), 3.33-4.10 (5H, m, 24-H2, 3-H, and THP), 4.76 (1H, m, THP), 5.38 (1H, m, 6-H). 19F-NMR δ: +43.3. MS m/z: 396 (M+ -DHP), 378.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 10 min
  3. extractionThe usual work-up (ether for extraction)
  4. customgave a crude product, which
  5. washElution with n-hexane-ether (5:1)

Sources & evidence

ORD record
ord-2447525ed53142b4a1bad178290ff743
Source dataset
uspto-grants-1986_01
Patent number
US04564474

Reaction notes

Loading…