Aluminium lithium hydride → HCID 10040611, compound

HRID 1639183Notes

Reaction equation

HRID 1639183 reaction equation
C([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]2[O:23]C(=O)C)[C@H:15]2[C@H:6]1[C:7]1[CH:8]=[CH:9][C:10]([O:27][CH3:28])=[CH:11][C:12]=1[CH2:13][CH2:14]2)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[OH:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]2[OH:23])[C@H:15]2[C@H:6]1[C:7]1[CH:8]=[CH:9][C:10]([O:27][CH3:28])=[CH:11][C:12]=1[CH2:13][CH2:14]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54407712HCID 54407712, compound

Product 1

HCID 10040611HCID 10040611, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the diacetate (25) (25 mg, 0.065 mmol) in dry ether (1 ml) was added to a stirred solution of lithium aluminium hydride (5 mg, 0.13 mmol) in dry ether (2 ml) at 0° C. under argon. After 15 min, excess lithium aluminium hydride was destroyed by addition of wet ether and then dropwise addition of water. The ethereal layer was separated, dried, and evaporated, and the residue was chromatographed on silica (1 g) to give the product (6) (18 mg, 91%), m.p. 161°-2° C. (from ether-light petroleum), νmax 3420 cm-1 (OH), δ (250 MHz), 7.21 (1 H, d, J 8 Hz, 1-proton), 6.76 (1 H, dd, J 8 and 2.5 Hz, 2-proton), 6.67 (1 H, d, J 2.5 Hz, 4-proton), 4.74 (1 H, m, 11-proton), 3.78 (3 H, s, OCH3), 3.71 (1 H, m, 17-proton), 2.86 (2 H, m, 7-protons), 2.44 (1 H, dd, J 11 and 2 Hz, 9-proton), 2.28 (1 H, dd, J 14 and 2.5 Hz, 12-proton), 2.11 (1 H, qt, J 11, 9, 2.5, and 2 Hz, 8-proton), 1.98-1.31 (7 H, m), 1.61 (2 H, br s OH), 1.03 (3 H, s, 18-CH3);

Workup

  1. customexcess lithium aluminium hydride was destroyed by addition of wet ether
  2. additiondropwise addition of water
  3. customThe ethereal layer was separated
  4. customdried
  5. customevaporated
  6. customthe residue was chromatographed on silica (1 g)

Sources & evidence

ORD record
ord-f2d924150108432ea4e13dcd2d13f12a
Source dataset
uspto-grants-1989_11
Patent number
US04882439

Reaction notes

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