Lithium tri-s-butylborohydride → HCID 22841016, compound

HRID 414777Notes

Reaction equation

HRID 414777 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[C@H:15]([OH:16])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>O1CCCC1>[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:15]([OH:16])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 13982256HCID 13982256, compound

Product 1

HCID 22841016HCID 22841016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Jones oxidation was carried out by the same procedure as described in Preparation 3, but using 2.22 g of dl-trans-2-benzyloxymethyl-3-hydroxytetrahydropyran (prepared as described in Preparation 6). The crude substance, 2.08 g, obtained in this way was dissolved in 10 ml of tetrahydrofuran, and 12 ml of a 1M tetrahydrofuran solution containing L-selectride were added dropwise to this solution at 0°-5° C. Using the same procedure and purification as described in Preparation 4, 1.135 g of the title compound was obtained as a colorless liquid, boiling at 130°-140° C. (bath temperature)/1 mmHg (133 Pa).

Workup

  1. customas described in Preparation 3
  2. customThe crude substance, 2.08 g, obtained in this way
  3. additionwere added dropwise to this solution at 0°-5° C
  4. customthe same procedure and purification
  5. customas described in Preparation 4

Sources & evidence

ORD record
ord-38bb6ad814c844aa9c552c6254d64ebb
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

Loading…