Diethyl Ether → 4,5,6,7-Tetrahydrobenzo[b]thiophene-3-carboxaldehyde

HRID 10224

Reaction equation

HRID 10224 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[C:3]([CH2:10][OH:11])=[CH:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(OCC)C.[OH-].[Na+]>ClCCl>[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[C:3]([CH:10]=[O:11])=[CH:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 219783784,5,6,7-Tetrahydro-1-benzothien-3-ylmethanol

Product 1

HCID 441227304,5,6,7-Tetrahydrobenzo[b]thiophene-3-carboxaldehydeYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4,5,6,7-tetrahydro-1-benzothien-3-ylmethanol (Step 1, 320 mg, 1.9 mmol) in dichloromethane (10 mL) was added to a stirred solution of 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (0.92 g, 2.1 mmol) in dichloromethane (10 mL) under nitrogen and stirred at room temperature for 20 minutes. Diethyl ether (50 mL) and 1N sodium hydroxide solution (25 mL) were added and the mixture stirred vigorously for 15 minutes. The organic layer was washed with sodium hydroxide, water and brine, dried over MgSO4 and evaporated in vacuo to give 4,5,6,7-tetrahydro-1-benzothiophene-3-carbaldehyde (280 mg, 88%). 1H NMR (360 MHz, CDCl3) δ 9.88 (1H, s), 7.85 (1H, s), 2.92–2.88 (2H, m), 2.76 (2H, t, J=6.0 Hz), 1.88–1.76 (4H, m).

Workup

  1. stirringthe mixture stirred vigorously for 15 minutes
  2. washThe organic layer was washed with sodium hydroxide, water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-68919c0526124ce58060d7db7429fb11
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Linked notes

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