HCID 14986530, compound → HCID 14986532, compound

HRID 257224Notes

Reaction equation

HRID 257224 reaction equation
[N:1]([CH:4]1[CH:9]([OH:10])[C:8]([CH3:12])([CH3:11])[O:7][C:6]2[CH:13]=[CH:14][S:15][C:5]1=2)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[NH2:1][CH:4]1[CH:9]([OH:10])[C:8]([CH3:11])([CH3:12])[O:7][C:6]2[CH:13]=[CH:14][S:15][C:5]1=2

Participants

4

Reactant 2

HCID 14986530HCID 14986530, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14986532HCID 14986532, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7-Azido-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran (2.0 g, 8.88 mmol) Was added carefully in small portions to a mixture of lithium aluminum hydride (0.67 g, 17.8 mmol) in diethyl ether (40ml). The resultant mixture was stirred an additional 1 h at rt and quenched with successive dropwise addition of water (0.7 ml), 15% aqueous sodium hydroxide (0.7 ml) and water (2.0 ml). The aluminum salts were removed by filtration and the ether solution was dried over magnesium sulfate. The solvent was evaporated in vacuo to give the product 1.64 g (93%) as a beige solid; mp 111°-116° C.; IR(KBr):3110, 2971, 1565 and 1403 cm-1 ; MS:m/z 200 (MH+); 1H NMR (CDCl3):δ 1.24(s,3H), 1.48(s,3H), 1.85(bs,3H, exchanges with D2O), 3.38 (d,J=8.6 Hz,1H), 3.70 (d,J=8.6 Hz,1H), 6.55 (d,J=5.4 Hz,1H) and 7.07(d,J=5.4 Hz,1H).

Workup

  1. customquenched with successive dropwise addition of water (0.7 ml), 15% aqueous sodium hydroxide (0.7 ml) and water (2.0 ml)
  2. customThe aluminum salts were removed by filtration
  3. dry with materialthe ether solution was dried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e4fe428c76e54e9286d21c4f0b30d13e
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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