Aluminium lithium hydride → HCID 69640853, compound

HRID 1744218Notes

Reaction equation

HRID 1744218 reaction equation
C([O:3][C:4]([C@@H:6]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:9]2([CH3:10])[C@@H:8]([O:26][CH2:27][O:28][CH3:29])[CH2:7]1)[C:20]1[CH:19]=[CH:18][C:17]([O:24][CH3:25])=[CH:16][C:15]=1[CH2:14][CH2:13]3)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[OH:3][CH2:4][C@@H:6]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:9]2([CH3:10])[C@@H:8]([O:26][CH2:27][O:28][CH3:29])[CH2:7]1)[C:20]1[CH:19]=[CH:18][C:17]([O:24][CH3:25])=[CH:16][C:15]=1[CH2:14][CH2:13]3

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86594473HCID 86594473, compound

Product 1

HCID 69640853HCID 69640853, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 53.7 mg (0.125 mmol) of 56 in anhydrous Et2O (2 mL) was stirred at rt as 47.3 mg (1.25 mmol) of LiAlH4 was added and reaction was stirred at rt for 2 h. The reaction mixture was poured into saturated Na—K tartrate (100 mL) and extracted with EtOAc (3×, 70 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo giving 47.1 mg (87%) of 57 as a clear colorless oil which was a single isomer as judged by 1H NMR and used without further purification in the next step. Data for 57: TLC, T-2, Rf 0.31; 1H NMR (400 MHz, CDCl3) δ 0.88 (s, 3H, H-18), 1.05 (t, 1H, J=10.6 Hz, H-14), 3.38 (s, 3H, —CH2OCH3), 3.42 (dd, 1H, J=10.3, 8.2 Hz, CH2OH), 3.60 (t, 1H, J=8.9 Hz, H-17α), 3.78 (s, 3H, ArOCH3), 3.89 (dd, 1H, J=10.3, 3.2 Hz, —CH2OH), 4.66 & 4.69 (AB quartet, 2H, JAB=6.5 Hz, OCH2O), 6.62 (d, 1H, J=2.6 Hz, H-4), 6.72 (dd, 1H, J=8.7, 2.6 Hz, H-2), 7.22 (d, 1H, J=8.7 Hz, H-1).

Workup

  1. additionwas added
  2. customreaction
  3. extractionextracted with EtOAc (3×, 70 mL)
  4. dry with materialCombined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5d72b814cfb4a7eb1967248374b91a4
Source dataset
uspto-grants-2006_03
Patent number
US07015211B2

Reaction notes

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