Tetrahydrofuran → HCID 57180402, compound

HRID 1899857Notes

Reaction equation

HRID 1899857 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:24]#[C:25][C:26]4[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1COCC1.CCCCCCC.[BH4-].[Na+]>O>[C:1]12([C:11]3[CH:12]=[C:13]([C:24]#[C:25][C:26]4[CH:27]=[CH:28][C:29]([CH2:30][OH:31])=[CH:32][CH:33]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8900HeptaneHCID 4311764Sodium borohydrideHCID 57007951HCID 57007951, compound

Product 1

HCID 57180402HCID 57180402, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

740 mg (1.6 mmol) of 4-[3-(1-adamantyl)-4-methoxyethoxymethoxyphenylethynyl]benzaldehyde were introduced into 40 ml of a mixture of THF and methanol (50/50) in a round-bottomed flask. 32 mg (0.8 mmol) of sodium borohydride were introduced in small amounts at 5° C. and the temperature was permitted to increase to room temperature. The reaction mixture was poured into water and extracted with ethyl acetate and the organic phase was separated by settling, dried over magnesium sulfate and evaporated.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-1158abc847e44cc2a50778afd4d7248e
Source dataset
uspto-grants-1996_11
Patent number
US05574036

Reaction notes

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