Water → HCID 21283460, compound

HRID 2232355Notes

Reaction equation

HRID 2232355 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][C:9]2[S:10][CH:11]=[CH:12][C:8]=2[CH:7]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:15]([O:3][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][C:9]2[S:10][CH:11]=[CH:12][C:8]=2[CH:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-ol

Product 1

HCID 21283460HCID 21283460, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of NaH (60% oil dispersion, 2.4 g, 0.06 mol) in DMF (50 ml) heated at 60° C. with stirring under N2 was added dropwise a solution of 5-(2-hydroxyethyl)benzo[b]thiophene (8.9 g, 0.05 mol) in DMF (50 ml). After 1/2 hour, a solution of benzyl bromide (10.3 g, 7.2 ml, d=1.438, 0.06 mol) in DMF (50 ml) was added dropwise. After 15 hours, the solution was poured into H2O and the aqueous phase extracted with ethyl acetate (3×). The organic layers were backwashed with H2O saturated NaCl, dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product was eluted with 10% (V/V) ethyl acetate-hexane to yield 9.7 g (72%) of product. The material was used directly in the next step without further purification.

Workup

  1. waitAfter 15 hours
  2. extractionthe aqueous phase extracted with ethyl acetate (3×)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed on silica gel
  7. washthe product was eluted with 10% (V/V) ethyl acetate-hexane

Sources & evidence

ORD record
ord-0fc98a57d0c145c98649b4e9d7d59ab8
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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