HCID 13391105, compound → HCID 13391106, compound

HRID 1153955Notes

Reaction equation

HRID 1153955 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH2:6][CH2:7][C:8]3[C:9]([C:14](O)=[O:15])=[CH:10][CH:11]=[CH:12][C:13]=3[C:2]1=2>O1CCCC1.O>[S:1]1[CH:5]=[CH:4][C:3]2[CH2:6][CH2:7][C:8]3[C:9]([CH2:14][OH:15])=[CH:10][CH:11]=[CH:12][C:13]=3[C:2]1=2

Participants

4

Reactant 1

HCID 13391105HCID 13391105, compound

Product 1

HCID 13391106HCID 13391106, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4,5-dihydronaphtho[1,2-b]thiophen-6-carboxylic acid (3.4 g, 0.015 mole) in 50 ml of tetrahydrofuran under an argon atmosphere was added dropwise borane-tetrahydrofuran complex (2.5 g, 0.030 mole). Upon complete addition, the reaction mixture was stirred at room temperature for 18.5 hours. The reaction mixture was then taken up in water and concentrated under reduced pressure to a residue. The residue was washed into a separatory funnel with aqueous 2N sodium hydroxide and methylene chloride. The aqueous layer was extracted with two 100 ml portions of methylene chloride. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 4,5-dihydronaphtho[1,2-b]thiophen-6-methanol; 2.8 g, mp 99°-100°.

Workup

  1. additionUpon complete addition
  2. concentrationconcentrated under reduced pressure to a residue
  3. washThe residue was washed into a separatory funnel with aqueous 2N sodium hydroxide and methylene chloride
  4. extractionThe aqueous layer was extracted with two 100 ml portions of methylene chloride
  5. dry with materialThe combined extracts were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fe248820d7c541c7917e58349265730f
Source dataset
uspto-grants-1984_12
Patent number
US04487778

Reaction notes

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