Acetic Acid → HCID 86658837, compound

HRID 447550Notes

Reaction equation

HRID 447550 reaction equation
[C:1]([C:3]1[S:7][C:6]([CH:8]=O)=[CH:5][CH:4]=1)#[CH:2].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl>[C:1]([C:3]1[S:7][C:6]([CH2:8][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1)#[CH:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 153942485-Ethynylthiophene-2-carbaldehyde

Product 1

HCID 86658837HCID 86658837, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-ethynylthiophene-2-carbaldehyde (88 mg, 0.646 mmol), morpholine (56 uL, 0.646 mmol) in 1,2-dichloroethane (3.0 mL) was added a drop of AcOH. The mixture was stirred for 15 min and then NaBH(OAc)3 (205 mg, 0.969 mmol) was added and stirred at room temperature for 18 h. The reaction was diluted with CH2Cl2 (30 mL) and washed with saturated NaHCO3 (2×5 mL), brine (5 mL), and the organic layer dried over MgSO4. The solvent was removed and the residue purified by column chromatography (silica gel, hexanes/EtOAc, 3:1) to give the title product (80 mg, 60%); MS ESI [M+H]+ 208.08, calcd for [C11H13NOS+H]+ 207.8.

Workup

  1. stirringstirred at room temperature for 18 h
  2. washwashed with saturated NaHCO3 (2×5 mL), brine (5 mL)
  3. dry with materialthe organic layer dried over MgSO4
  4. customThe solvent was removed
  5. customthe residue purified by column chromatography (silica gel, hexanes/EtOAc, 3:1)

Sources & evidence

ORD record
ord-3cff5dd02c3c41659b563345ea5a0e09
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Reaction notes

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