Diethyl Ether → HCID 15661021, compound

HRID 1087387Notes

Reaction equation

HRID 1087387 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH: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]([OH:18])=O)[CH:2]=1.C[Li].[CH3:21]COCC.[Cl-].[NH4+]>C1COCC1>[C:16]([C:3]1[CH:2]=[CH:1][C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=1)(=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 9795017HCID 9795017, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 15661021HCID 15661021, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of dibenzo[b,f]thiepin-3-carboxylic acid (U.S. Pat. No. 4,536,507 (1985)) (415 mg, 1.63 mmole) in THF (20 mL) at 0° C. there was added methyl lithium in ether 1.4M (2.56 mL, 3.59 mmol); the mixture was stirred at 0° C. for 1 hour, then poured onto a well-stirred saturated aqueous ammonium chloride solution (100 mL). The organic phase was collected, washed twice with brine, dried and evaporated. Column chromatography on silica gel, eluting with a 1:2 mixture of ethyl acetate-hexane, afforded the title compound as a yellow solid (320 mg), m.p.: 82°-84° C.

Workup

  1. customThe organic phase was collected
  2. washwashed twice with brine
  3. customdried
  4. customevaporated
  5. washColumn chromatography on silica gel, eluting with a 1:2 mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-78670556aeed4019812c485d5d663bfb
Source dataset
uspto-grants-1991_07
Patent number
US05036067

Reaction notes

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