Hydrochloric Acid → HCID 66750770, compound

HRID 643925Notes

Reaction equation

HRID 643925 reaction equation
[CH2:1]([O:8][C:9]1[C:10](Br)=[CH:11][C:12]2[CH2:16][CH:15]([CH3:17])[S:14][C:13]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[B:25](OC)([O:28]C)[O:26]C.Cl>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]1[C:10]([B:25]([OH:28])[OH:26])=[CH:11][C:12]2[CH2:16][CH:15]([CH3:17])[S:14][C:13]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 66750593HCID 66750593, compoundHCID 178418339Butyllithium

Product 1

HCID 66750770HCID 66750770, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-benzyloxy-5-bromo-2-methyl-2,3-dihydrobenzo[b]thiophene (1.0 g, 3.0 mmol) in THF at 0° C. is added n-BuLi (1.8 mL, 4.5 mmol, 2.5 M in hexane) and the mixture is stirred for 1.5 h at 0° C. B(OMe)3 (1.67 mL, 15 mmol) is added dropwise and it is warmed to RT and stirred for 1.5 h. 3M HCl solution is added slowly at 0° C. and EtOAc is added to extract the product. The organic phase is dried with MgSO4 and concentrated. The residue is purified by chromatography to give the title compound as a white solid: (M+H)+=301.

Workup

  1. temperatureit is warmed to RT
  2. stirringstirred for 1.5 h
  3. extractionto extract the product
  4. dry with materialThe organic phase is dried with MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-eeff7369894d4c7eb18b683f28e2a84d
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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