Water → 5,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

HRID 1354025Notes

Reaction equation

HRID 1354025 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[N:10]O)[CH2:7][CH2:8][CH2:9][C:2]1=2.[H-].C([Al+]CC(C)C)C(C)C.[F-].[Na+].O>ClCCl>[S:1]1[C:2]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:10][C:3]=2[CH:4]=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 29898N-(4,5,6,7-tetrahydro-1-benzothiophen-4-ylidene)hydroxylamineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepineYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6,7-dihydro-5H-benzo[b]thiophen-4-one oxime (1.67 g) in dry dichloromethane (100 mL) was cooled to 0°. Following dropwise addition of diisobutylaluminum hydride (50 ml, 1M in hexanes), the mixture was stirred at 0° for three hours and then diluted with dichloromethane (50 mL). Sodium fluoride (8.4 g) was added, followed by water (2.7 mL). The reaction mixture was stirred vigorously for 30 minutes, then filtered and concentrated to provide the title compound (0.81 g) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred vigorously for 30 minutes
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-315aa942c4ac4b3abd33bc300456a1ef
Source dataset
uspto-grants-2007_05
Patent number
US07223752B2

Reaction notes

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