Diboron → 3-Hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin

HRID 1732351Notes

Reaction equation

HRID 1732351 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[C:3]([C:16](O)=[O:17])[CH:2]=1.B#B>O1CCCC1.O>[OH:17][CH2:16][C:3]1[CH:2]=[CH:1][C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 6328200DiboronHCID 13151858HCID 13151858, compound

Product 1

HCID 202555023-Hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 7.5 gm. of 10,11-dihydrodibenzo[b,f]-thiepin-3-carboxylic acid in 140 ml. of tetrahydrofuran. With stirring, add 90 ml. of 1 N diborane in tetrahydrofuran. Stir at room temperature for 2 hours and dilute the reaction mixture with water. Extract into ether, and evaporate the ether extract to dryness. Stir the residue with hexane and filter to obtain the title product (m.p., 82°-84° C.).

Workup

  1. dissolutionDissolve 7.5 gm
  2. additionadd 90 ml
  3. stirringStir at room temperature for 2 hours
  4. extractionExtract into ether
  5. customevaporate the ether
  6. extractionextract to dryness
  7. stirringStir the residue with hexane
  8. filtrationfilter

Sources & evidence

ORD record
ord-b0b2b82bec164028997e437c011ae2bf
Source dataset
uspto-grants-1980_12
Patent number
US04237160

Reaction notes

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