Hydrochloric Acid → HCID 59515213, compound

HRID 339624Notes

Reaction equation

HRID 339624 reaction equation
[Li]CCCC.CCCCCC.Br[C:13]1[C:26]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:25][CH:24]=[CH:23][C:14]=1[CH2:15][O:16]C1CCCCO1.[B:37](OC(C)C)(OC(C)C)[O:38]C(C)C.Cl>C1COCC1>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][O:27][C:26]2[C:13]3[B:37]([OH:38])[O:16][CH2:15][C:14]=3[CH:23]=[CH:24][CH:25]=2)=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 595152152-[2-Bromo-3-(4-methoxy-benzyloxy)-benzyloxy]-tetrahydro-pyranHCID 178418339Butyllithium

Product 1

HCID 59515213HCID 59515213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2.5 M n-BuLi in hexane (1.53 mL, 3.83 mmol) was added dropwise to a solution of 2-[2-bromo-3-(4-methoxy-benzyloxy)-benzyloxy]-tetrahydro-pyran (1.3 g, 3.2 mmol) in THF (14 mL) under N2 at −78° C. (bath temp). The mixture was stirred at −78° C. (bath temp) for 2 h then triisopropyl borate (0.90 mL, 3.8 mmol) was added slowly and stirred at −78° C. (bath temp) for 4 h. The mixture was allowed to warm up to 0° C. (bath temp) and then acidified with 3 M HCl to pH 5. The mixture was stirred for 3 h and the resulting precipitate was isolated by filtration and washed with 1:9 CH2Cl2/Et2O to give A25 as a yellow solid: yield 0.10 g (12%).

Workup

  1. stirringstirred at −78° C. (bath temp) for 4 h
  2. temperatureto warm up to 0° C. (bath temp)
  3. stirringThe mixture was stirred for 3 h
  4. customthe resulting precipitate was isolated by filtration
  5. washwashed with 1:9 CH2Cl2/Et2O
  6. customto give A25 as a yellow solid

Sources & evidence

ORD record
ord-6e110944a8f14581b2bef486fe1ef8f5
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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